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Chemical Structure| 341-23-1 Chemical Structure| 341-23-1
Chemical Structure| 341-23-1

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CAS No.: 341-23-1

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Product Details of [ 341-23-1 ]

CAS No. :341-23-1
Formula : C7H5FN2
M.W : 136.13
SMILES Code : FC1=C2C(=CC=C1)[NH]N=C2
MDL No. :MFCD07371561
InChI Key :YTNDJUBXSVSRQK-UHFFFAOYSA-N
Pubchem ID :22477757

Safety of [ 341-23-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Calculated chemistry of [ 341-23-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 9
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 36.05
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

28.68 ?2

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.04
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

1.65
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

2.12
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

1.56
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

2.5
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.77

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-2.39
Solubility 0.555 mg/ml ; 0.00408 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-1.87
Solubility 1.85 mg/ml ; 0.0136 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-3.16
Solubility 0.0944 mg/ml ; 0.000693 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

 High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

 Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

 No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

 Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

 No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

 No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

 No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

 No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.96 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

 0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

 None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

 0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

 0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

 1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

 No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

 1.58

Application In Synthesis of [ 341-23-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 341-23-1 ]

[ 341-23-1 ] Synthesis Path-Downstream   1~27

  • 1
  • [ 388-22-7 ]
  • [ 341-23-1 ]
  • 2
  • 2,6-difluoro-benzaldehyde <i>O</i>-methyl-oxime [ No CAS ]
  • [ 341-23-1 ]
  • 3
  • [ 443-86-7 ]
  • [ 341-23-1 ]
  • 7
  • [ 110-87-2 ]
  • [ 341-23-1 ]
  • [ 1178903-32-6 ]
  • 8
  • [ 110-87-2 ]
  • [ 341-23-1 ]
  • [ 1178903-43-9 ]
  • 9
  • [ 341-23-1 ]
  • [ 824-94-2 ]
  • [ 1178903-31-5 ]
  • [ 1178903-42-8 ]
  • 10
  • [ 341-23-1 ]
  • [ 105-13-5 ]
  • [ 1178903-31-5 ]
  • 11
  • [ 341-23-1 ]
  • [ 212051-17-7 ]
  • [ 1178903-31-5 ]
  • [ 1178903-42-8 ]
  • 12
  • [ 341-23-1 ]
  • [ 518990-32-4 ]
YieldReaction ConditionsOperation in experiment
86.5% With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20℃; for 2h; Example IB Preparation of 4-(l-(2-chloro-6-(trifluoromethyl)benzoyl)-4-fluoro-lH-indazol-3- yl)cyclohex-3-enecarboxylic acid (IB) Step 1: Preparation of 4-fluoro-3-iodo-1H-indazole (B-2). A solution of <strong>[341-23-1]4-fluoroindazole</strong> (B-l) (5.00 g, 36.73 mmol) in DMF (80 mL) was added I2 (18.64 g, 73.46 mmol) and KOH (7.73 g, 137.7 mmol) successively at room temperature under stirring. After 2 hours, TLC showed that the reaction was completed, the reaction mixture was poured into aq. NaHS03 (10%, 200 mL) and extracted with EA (3x200 mL). The combined organic layers were washed with H20 (100 mL) and brine (2x200 mL), dried over anhydrous Na2S04, filtered and concentrated, the crude solid was washed with PE to give a yellow solid B-2 (8.33 g), yield 86.5%. Physical characterization data for B-2 is as follows: LCMS(ESI): calc. C7H4FIN2, 261.9; obs. M+H=262.9
86.5% With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20℃; for 2h; Step 1: Preparation of 4-fluoro-3-iodo-1H-indazole (B-2). To a solution of <strong>[341-23-1]4-fluoroindazole</strong> (B-i) (5.00 g, 36.73 mmol) in DMF (80 mL), was added 12 (18.64 g, 73.46mmol) and KOH (7.73 g, 137.7 mmol) at room temperature while stirring. After 2 hours,TLC indicated that the reaction was complete. The reaction mixture was poured into aq.NaHSO3 (10%, 200 mL) and extracted with EA (3x200 mL). The combined organic layer was washed with H20 (100 mL) and brine (2x200 mL), dried over anhydrous Na2SO4, filtered and concentrated. The crude (solid) was washed with PE to give a yellow solid B-2 (8.33 g), yield 86.5%. Physical characterization data for B-2 was as follows: LCMS(ESI): calc.C7H4FIN2, 261.9; obs. M+H=262.9
86.5% With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20℃; for 2h; Step 1: Preparation of 4-fluoro-3-iodo-1H-indazole (B-2) [0309] To a solution of <strong>[341-23-1]4-fluoroindazole</strong> (B-1) (5.00 g, 36.73 mmol) in DMF (80 mL), was added I2 (18.64 g, 73.46 mmol) and KOH (7.73 g, 137.7 mmol) at room temperature while stirring. After 2 hours, TLC indicated that the reaction was complete. The reaction mixture was poured into aq. NaHSO3 (10%, 200 mL) and extracted with EA (3×200 mL). The combined organic layer was washed with H2O (100 mL) and brine (2×200 mL), dried over anhydrous Na2SO4, filtered and concentrated. The crude (solid) was washed with PE to give a yellow solid B-2 (8.33 g), yield 86.5%. Physical characterization data for B-2 was as follows: LCMS(ESI): calc. C7H4FIN2, 261.9; obs. M+H=262.9.
83% With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20℃; A suspension of <strong>[341-23-1]4-fluoro-1H-indazole</strong> (500 mg, 3.67 mmol, 1.00 equiv), iodine (1.87 g, 2.00 equiv) and potassium hydroxide (741 mg, 13.21 mmol, 3.60 equiv) in N,N-dimethylformamide (5mL) was stirred overnight at room temperature. The reaction was quenched by 10% aqueous NaHSO3, extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. The resulting solid was washed with petroleum ether to give 800 mg (83%) of the title compound as a yellow solid. LC-MS (ES, m/z): 263 [M+H].
65% With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 0 - 20℃; To a solution of 4-fluoro-lH-indazole (i-3a) (24 g, 180 mmol) in DMF (300ml) was added iodine (56 g, 216 mmol) and KOH (40 g, 720 mmol) at 0C. The resultant mixture was allowed to warm to room temperature and stirred for 5 h. The reaction mixture was slowly quenched with saturated sodium thiosulfate (200 mL) and extracted with EtOAc (500 mL x 3). The combined organic layers were washed, dried and concentrated, and the residue was purified by re-crystallization to afford the title compound (30 g, yield: 65%). LCMS (ESI) calc'd for C7H4FIN2 [M+H]+: 263, found: 263.
65% With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 0 - 20℃; for 5h; Step 1. Preparation of 4-fluoro-3-iodo-1H-indazole (i-7a).To a solution of <strong>[341-23-1]4-fluoro-1H-indazole</strong> (24 g, 180 mmol) in 300 mL of DMF was added diiodine (56 g, 216 mmol) and potassium hydroxide (40 g, 720 mmol) at 0 C. The resultant mixture was allowed to warm to room temperature and stirred for 5 hours. The reaction mixture was slowly quenched with saturated sodium thiosulfate (200 mL) and extracted with EA (500 mL * 3), and the combined organic layers were washed, dried and concentrated. Theresidue was purified by re-crystallization to afford the title compound (30 g, yield: 65%). LCMS (ESI) calc?d for C7H4FIN2 [M+H]: 263, found: 263.
65% With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 0℃; for 20h; i). Preparation of 4-fluoro-3-iodo-1H-indazole (i-3b) To a solution of <strong>[341-23-1]4-fluoro-1H-indazole</strong> (i-3a) (24 g, 180 mmol) in DMF (300 ml) was added iodine (56 g, 216 mmol) and KOH (40 g, 720 mmol) at 0 C. The resultant mixture was allowed to warm to room temperature and stirred for 5 h. The reaction mixture was slowly quenched with saturated sodium thiosulfate (200 mL) and extracted with EtOAc (500 mL*3). The combined organic layers were washed, dried and concentrated, and the residue was purified by re-crystallization to afford the title compound (30 g, yield: 65%). LCMS (ESI) calc'd for C7H4FIN2 [M+H]+: 263. found: 263.
With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20℃; for 2h; Example 24A: Preparation of sodium 4-(l-(2-chloro-6-(trifluoromethyl) benzoyl)-4- fluoro-/H-indazol-3-yl)-3-fluorobenzoate (24A)A-5 A-6 24A i) Preparation of 4-fluoro-3-iodo-/H-indazole (A-2). To a solution of <strong>[341-23-1]4-fluoroindazole</strong> A-l (5.00 g, 36.7 mmol) in DMF (80 mL) was added h (18.6 g, 73.5 mmol) and KOH (7.73 g, 134 mmol) successively at rt. After 2 h, the reaction mixture was poured into aq. 10% NaHS03 (200 mL) and extracted with EtOAc (200 mL*3). The combined organic layers were washed with H20 and brine, dried over Na2S04, and concentrated. The crude solid was washed with PE to give the title compound as a yellow solid. LCMS (ESI) calc'd for C7H5FIN2 [M+H]+: 262.9, found: 262.9

  • 13
  • [ 341-23-1 ]
  • (2-chloro-6-(trifluoromethyl)phenyl)(4-fluoro-3-iodo-1H-indazol-1-yl)methanone [ No CAS ]
  • 14
  • [ 341-23-1 ]
  • methyl 4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-4-fluoro-1H-indazol-3-yl)-3-fluorobenzoate [ No CAS ]
  • 15
  • [ 341-23-1 ]
  • 4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-4-fluoro-1H-indazol-3-yl)-3-fluorobenzoic acid [ No CAS ]
  • 16
  • [ 341-23-1 ]
  • sodium 4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-4-fluoro-1H-indazol-3-yl)-3-fluorobenzoate [ No CAS ]
  • 19
  • [ 341-23-1 ]
  • [ 350-46-9 ]
  • [ 1438463-92-3 ]
  • 20
  • [ 341-23-1 ]
  • [ 885521-60-8 ]
YieldReaction ConditionsOperation in experiment
69% With bromine; sodium hydroxide; at 20℃; for 3h; Example i-3: Preparation of (3-bromo-4-fluoro-1H-indazol-l-yl)(2-chloro-6- (trifluoromethyl)phenyl)methanone Scheme i-3 Step 1. Preparation of 3-bromo-4-fluoro-lH-indazole (i-3b). To a suspension of 4-fluoro- lH-indazole (i-3a) (5 g, 36.8 mmol) in 2M sodium hydroxide solution (100 ml) at rt was added a solution of bromine(5.8 g, 36.8 mmol) in 2M sodium hydroxide solution(60 ml). The reaction mixture was stirred at r.t. for 3h. To the reaction mixture was added sodium bisulfite aqueous solution (10%, lOOmL). The solution was extracted with Ethyl Acetate (2xl50mL). the combined Organic Layer was washed with H20 (3xl00mL) and Brine (2xl50mL). the solution was dried over anhydrous Na2S04 and evaporated. 5.47g product was obtained. Yield 69%. LCMS (ESI) calc'd for C7H4BrFN2 [M+H]+: 215, found: 215.
69% With bromine; sodium hydroxide; In water; at 20℃; for 3h; Step 1. Preparation of 3-bromo-<strong>[341-23-1]4-fluoro-1H-indazole</strong> (i-3b). To a suspension of 4-fluoro- 1H-indazole (i-3a) (5 g, 36.8 mmol) in 2M sodium hydroxide solution (100 ml) at room temperature was added a solution of bromine(5.8 g, 36.8 mmol) in 2M sodium hydroxidesolution (60 ml). The reaction mixture was stirred at room temperature for 3h. To the reaction mixture was added sodium bisulfite aqueous solution (10%, lOOmL). The solution was extracted with ethyl acetate (2xl5OmL). The combined organic layer was washed with H20 (3xlOOmL) and brine (2xl5OmL). The solution was dried over anhydrous Na2SO4 and evaporated. 5.47g product was obtained. Yield 69%. LCMS (ESI) calc?d for C7H4BrFN2[M+H]: 215, found: 215.
69% With bromine; sodium hydroxide; In water; at 20℃; for 3h; To a suspension of 4-fluoro- lH-indazole (i-2a) (5 g, 36.8 mmol) in 2M sodium hydroxide solution (100 ml) at r.t. was added a solution of bromine (5.8 g, 36.8 mmol) in 2M sodium hydroxide solution(60 ml). The reaction mixture was stirred at r.t. for 3 hr. To the reaction mixture was added sodium bisulfite aqueous solution (10%, lOOmL). The solution was extracted with Ethyl Acetate (2xl50mL). The combined Organic Layer was washed with H20 (3xl00mL) and Brine (2xl50mL). The solution was dried over anhydrous Na2S04 and evaporated. 5.47g product was obtained. Yield 69%. LCMS (ESI) calc'd for C7H4BrFN2 [M+H]+: 215, found: 215.
69% With bromine; sodium hydroxide; at 20℃; for 3h; Step 1. Preparation of 3-bromo-<strong>[341-23-1]4-fluoro-1H-indazole</strong> (i-2b). To a suspension of 4-fluoro- 1H-indazole (i-2a) (5 g, 36.8 mmol) in 2M sodium hydroxide solution (100 ml) at room temperature was added a solution of bromine (5.8 g, 36.8 mmol) in 2M sodium hydroxide solution(60 ml). The reaction mixture was stirred at room temperature for 3 hr. To thereaction mixture was added sodium bisulfite aqueous solution (10%, 1 OOmL). The solution was extracted with ethyl acetate (2xl5OmL). The combined organic layer was washed with H20 (3xlOOmL) and brine (2xl5OmL). The solution was dried over anhydrous Na2SO4 and evaporated. 5.47g product was obtained. Yield 69%. LCMS (ESI) calc?d for C7H4BrFN2 [M+H]: 215, found: 215.
69% With bromine; sodium hydroxide; In water; at 20℃; for 3h; Step 1. Preparation of 3-bromo-<strong>[341-23-1]4-fluoro-1H-indazole</strong> (i-3b) [0267] To a suspension of <strong>[341-23-1]4-fluoro-1H-indazole</strong> (i-3a) (5 g, 36.8 mmol) in 2M sodium hydroxide solution (100 ml) at room temperature was added a solution of bromine (5.8 g, 36.8 mmol) in 2M sodium hydroxide solution (60 ml). The reaction mixture was stirred at room temperature for 3 h. To the reaction mixture was added sodium bisulfite aqueous solution (10%, 100 mL). The solution was extracted with ethyl acetate (2×150 mL). The combined organic layer was washed with H2O (3×100 mL) and brine (2×150 mL). The solution was dried over anhydrous Na2SO4 and evaporated. 5.47 g product was obtained. Yield 69%. LCMS (ESI) calc'd for C7H4BrFN2 [M+H]+: 215. found: 215.

  • 22
  • [ 341-23-1 ]
  • [ 1561949-67-4 ]
  • 24
  • [ 341-23-1 ]
  • C23H17ClF4N2O3 [ No CAS ]
  • 25
  • [ 341-23-1 ]
  • [ 1562375-26-1 ]
  • [ 1562375-27-2 ]
  • 26
  • [ 341-23-1 ]
  • [ 1562374-41-7 ]
  • 27
  • [ 341-23-1 ]
  • [ 1562375-05-6 ]
 

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