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[ CAS No. 192702-01-5 ] {[proInfo.proName]}

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Chemical Structure| 192702-01-5
Chemical Structure| 192702-01-5
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Product Details of [ 192702-01-5 ]

CAS No. :192702-01-5 MDL No. :MFCD01631551
Formula : C7H5BrClF Boiling Point : No data available
Linear Structure Formula :- InChI Key :GGTQWWTYUKXFPP-UHFFFAOYSA-N
M.W : 223.47 Pubchem ID :2757542
Synonyms :

Calculated chemistry of [ 192702-01-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 44.25
TPSA : 0.0 ?2

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.06 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.34
Log Po/w (XLOGP3) : 3.66
Log Po/w (WLOGP) : 3.64
Log Po/w (MLOGP) : 4.1
Log Po/w (SILICOS-IT) : 3.89
Consensus Log Po/w : 3.53

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.91
Solubility : 0.0275 mg/ml ; 0.000123 mol/l
Class : Soluble
Log S (Ali) : -3.35
Solubility : 0.1 mg/ml ; 0.000448 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.56
Solubility : 0.0062 mg/ml ; 0.0000277 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.84

Safety of [ 192702-01-5 ]

Signal Word:Danger Class:8
Precautionary Statements:P264-P271-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P403+P233-P501 UN#:3265
Hazard Statements:H314 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 192702-01-5 ]

* 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 [ 192702-01-5 ]

[ 192702-01-5 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 1513-25-3 ]
  • [ 192702-01-5 ]
  • 2
  • [ 192702-01-5 ]
  • [ 1068-90-2 ]
  • [ 14937-92-9 ]
  • 3
  • [ 123-56-8 ]
  • [ 192702-01-5 ]
  • 1-(3-chloro-4-fluorobenzyl)pyrrolidine-2,5-dione [ No CAS ]
  • 4
  • [ 186202-57-3 ]
  • [ 192702-01-5 ]
  • [ 610779-90-3 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; for 18h; Description 16: [(2S)-4-(3-Chloro-4-fluoro-benzvl) morpholin-2-vimethVllcarbamic acid ter-butyl ester A solution of (R)- (2-morpholinylmethyl)-carbamic acid 1, 1-dimethyl ester [CAS 186202-57-3] (0.26g) in dichloromethane (5ml) was treated with triethylamine (0. 167ml) and <strong>[192702-01-5]3-chloro-4-fluorobenzyl bromide</strong> (0.27g). After stirring for 18hrs the mixture was purified by applying directly to an SCX ion exchange cartridge (10g), eluting with methanol followed by 10% 0.880 ammonia/methanol. The basic fraction was evaporated in vacuo to give the title compound (0.37g) as a colourless gum. LC-MS: Rt = 2.46min. Mass Spectrum m/z 359 [MH+]
  • 5
  • [ 192702-01-5 ]
  • [ 123-54-6 ]
  • [ 1001072-25-8 ]
YieldReaction ConditionsOperation in experiment
92% INTERMEDIATE 7; Synthesis of 3-(3-chloro-4-fluorobenzyl)pentane-2,4-dione; A mixture of pentane-2,4-dione (2.00 g, 10.0 mmol), 4-(bromomethyl)-2-chloro-l- fluorobenzene (2.23 g, 10.0 mmol) and Li2CO3 (1.48 g, 20.0 mmol) was heated in DMF (30 mL) at 75 0C for 1 h. The mixture was then poured on sat NaCl and acidified with sat HCl. Toluene (100 mL) was used to extract the product. The organic phase was washed twice with sat NaCl, dried (Na2SO4), filtered and evaporated to 2.16 g (92%) clear oil, pure as a tautomeric mixture. MS (ESI) m/z 236 [M+H+].
  • 6
  • [ 192702-01-5 ]
  • (6S)-2-(3-chloro-4-fluorobenzyl)-8-ethyl-10-methoxy-N,6-dimethyl-1,9-dioxo-1,2,6,7,8,9-hexahydropyrazino[1',2':1,5]pyrrolo[2,3-d]pyridazine-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
To a cold (0 C) solution of (6S)-8-ethyl-10-methoxy-N,6-dimethyl-1,9-dioxo- l ,2,6,7,8,9-hexahydropyrazino[ 1 ',2': 1 ,5]pyrrolo[2,3-d]pyridazine-4-carboxamide (1.58 g, 4.73 mmol) in anhydrous DMF (50 mL), a solution of lithium bis (trimethylsilyl)amide mL, 4.97 mmol, 1 M in THF) was added. After stirring at the same temperature for 25 minutes, <strong>[192702-01-5]3-chloro-4-fluorobenzyl bromide</strong> (1.27 g, 5.68 mmol) was added. The reaction mixture was stirred at room temperature for 10 minutes and concentrated under vacuum. The residue was partitioned between chloroform and brine. The organic extract was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with a 1-5% methanol in ethyl acetate gradient. Collection and concentration of appropriate fractions provided the title compound. 1H NMR (400 MHz, CDC13) 6 7.46 (dd, J = 6.9, 2.2 Hz, 1H), 7.32 (m, 1H), 7.09 (t, J = 7.6 Hz, 1H), 7.03 (br signal, 1H), 5.92 (m, 1H), 5.32 (d, J = 14.1 Hz, 1H), 5.26 (d, J = 14.1 Hz, 1H), 4.14 (s, 3H), 3.97 (dd, J = 13.2, 3.7 Hz, 1H), 3.73 (heptet, J = 7.2 Hz, 1 H), 3.51 (heptet, J = 7.1 Hz, 1H), 3.21 (dd, J = 13.2, 1.7 Hz, 1H), 3.03 (d, J = 5.0 Hz, 3H), 1.42 (d, J = 6.6 Hz, 3H), 1.23 (t, J = 7.1 Hz, 3H). ES MS M+1 = 476
  • 7
  • [ 192702-01-5 ]
  • [ 870006-84-1 ]
YieldReaction ConditionsOperation in experiment
To a solution of (65)-4-amino-8-ethyl-1 0-methoxy-6-methyl-7,8- dihydropyrazino[1',2':1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione (0.94 g, 3.23 mmol) in anhydrous DMF (32 mL) under an atmosphere of nitrogen, a solution of lithium bis (trimethylsilyl)amide THF (3.87 mL, 1 M, 3.87 mmol) was added. The mixture was stirred at room temperature for 15 minutes and treated with <strong>[192702-01-5]4-fluoro-3-chlorobenzyl bromide</strong> (0.72 g, 3.23 mmol). The reaction mixture was stirred at room temperature for 1 hour and concentrated under vacuum. The residue was partitioned between chloroform and dilute hydrochloric acid. The organic extract was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with 0-20% methanol in ethyl acetate gradient. Collection and concentration of appropriate fractions provided the title material. 1H NMR (400 MHz, DMSO-d6) No. 7.46 (dd, J = 7.2, 2.0 Hz, 1H), 7.37 (t, J = 8.7 Hz, 1H), 7.27 (m, 1H), 5.57 (s, 2H), 5.19 (m, 1H), 5.11 (d, J = 14.7 Hz, 1H), 5.03 (d, J = 14.7 Hz, 1H), 3.91 (s, 3H), 3.89 (m, 1H), 3.65 (heptet, J = 6.4 Hz, 1 H), 3.37 (m), 1.32 (d, J = 6.6 Hz, 3H), 1.11 (t, J = 7.2 Hz, 3H). ES MS M+1 = 434
  • 8
  • [ 7770-45-8 ]
  • [ 192702-01-5 ]
  • [ 925442-48-4 ]
YieldReaction ConditionsOperation in experiment
81% Sodium hydride (97.0 mg, 2.22 mmol) was suspended in N,N-dimethylformamide (10 mL) in a nitrogen atmosphere, and the suspension was cooled to 0C. 4-Hydroxy-1-naphthaldehyde (252 mg, 1.46 mmol) was slowly added, and the mixture was stirred at 0C for 30 minutes. 4-(Bromomethyl)-2-chloro-1-fluorobenzene (480 mg, 2.15 mmol) was further added, and the mixture was stirred at room temperature for three hours. A dilute hydrochloric acid solution (30 mL) was added to the reaction solution, followed by extraction with ethyl acetate (50 ml). The organic layer was washed with brine and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate = 20/1 to 3/1) to give the target compound (371 mg, yield: 81%) as a light yellow solid. 1H-NMR (CDCl3, 500MHz):delta ppm: 5.29 (2H, s), 6.97 (1H, d, J=7.8Hz), 7.22 (1H, t, J=8.5Hz), 7.40 (1H, m), 7.58-7.62 (2H, m), 7.73 (1H, m), 7.92 (1H, d, J=8.3Hz), 8.37 (1H, d, J=8.8Hz), 9.32 (1H, d, J=8.8Hz), 10.23 (1H, s). MS (EI) m/z: 314.0511 (M+)
  • 9
  • [ 192702-01-5 ]
  • [ 7731-00-2 ]
  • 10
  • [ 452-84-6 ]
  • [ 192702-01-5 ]
  • 11
  • [ 161446-90-8 ]
  • [ 192702-01-5 ]
YieldReaction ConditionsOperation in experiment
With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0 - 20℃; [00202] A solution of 3-chloro-4-fluorobenzaldehyde (3 g) in THF (40 ml) was added over 2 minutes to a stirred suspension of sodium borohydride (1.07 g) in methanol (40 ml) at 0 C. The mixture was allowed to warm to room temperature and then quenched with water. The resulting suspension was partitioned between water and diethyl ether and the combined organic extracts were dried and concentrated in vacuo. The residue was dissolved in dichloromethane (90 ml) and triphenylphosphine (4.62 g) and tetrabromomethane (6.64 g) were added at 0 C. The mixture was allowed to warm to room temperature overnight then concentrated in vacuo and the residue purified by column chromatography using iso-hexane as eluent to yield the desired product (3.57 g, 85%). NMR: delta 4.7 (s, 2H), 7.4 (m, 2H), 7.7 (m, 1H).
With carbon tetrabromide; triphenylphosphine; In dichloromethane; for 3h; Intermediate 50 (1.25 mmol), triphenylphosphine (1.87 mmol) and carbon tetrabromide (1.87 mmol) were stirred in anhydrous DCM, under nitrogen for 3 hours. The solvent was removed under reduced pressure and the crude material was purified by chromatography on silica gel to give intermediate 51, which was a colourless oil. Intermediate 51 was characterized by the following spectroscopic data: 1H NMR (DMSO-d6, 400 MHz) (ppm) 4.43 (s, 2H), 7.13 (t, J=8.37 Hz, 1H), 7.26-7.28 (m, 1H), 7.44-7.47 (d, J=6.70 Hz, 1H).
With phosphorus tribromide; In dichloromethane; at 0 - 20℃; for 1h;Inert atmosphere; To a solution of (3-chloro-4-fluoro-phenyl)-methanol (4.3 g, 26.8 mmol) in DCM (20 mL) was added PBr3 (1 mL) at 0 C. The resulting mixture was stirred at room temperature for 1 hour before it was quenched with satd. aq. NaHC03 solution. The organic solution was washed with water, brine, dried over anhy. Na2S04 and concentrated in vacuo to give the desired product (3.7 g, 61.9%). It was used directly in the next step, without further purification
  • 12
  • [ 865300-47-6 ]
  • [ 192702-01-5 ]
  • [ 865300-48-7 ]
YieldReaction ConditionsOperation in experiment
Step 3: 6- (3-chloro-4-fluorobenzyl)-4-hydroxy-N, N, 2-trimethyl-3, 5-oxo-2, 3,5, 6,7, 8- hexahydro-2, 6-naphthyridine-1-carboxamide; A solution of 4-hydroxy-N, N, 2-trimethyl-3,5-dioxo-2, 3,5, 6,7, 8-hexahydro-2,6- naphthyridine-1-carboxamide (0. 018g, 0.068 mmol) in DMF (2 mL) was treated with Cs2C03 (0. 066g, 0.2 mmol) and 3-chloro-4-fluoro benzyl bromide (0. 045g, 0. 2 mmol) and heated to 40 C. The reaction mixture was then cooled to 0 degrees C, a suspension of NaH (95% dispersion in oil, 0. 2 mmol) was added and the reaction was warmed to room temperature. After 1 hr the reaction was partitioned between ice water and EtOAc, the organic layer was dried with brine and Na2SO4, filtered and evaporated to give 6- (3-chloro-4-fluorobenzyl)-4- [ (3-chloro-4-fluorobenzyl) oxy] -N, N, 2-trimethyl-3, 5- dioxo-2, 3,5, 6,7, 8-hexahydro-2, 6-naphthyridine-1-carboxamide (ES MS M+1= 549.9). This material was then dissolved in CH2C12 (3 mL) and treated with 4 drops of a 30% by weight solution of HBr in propionic acid at room temperature. After 20 minutes the solution was concentrated and purified by reverse phase chromatography to give the product. 1HNMR (400 M : Hz, CD30Do o 7.48 (m, 1H), 7.32 (m, 1H), 7.22 (t, J=8. 5 Hz, 1H), 4.76 (d, J=14. 8 Hz, 1H), 4.63 (d, J=14. 8 Hz, 1H), 3.50 (t, J=6. 4 Hz, 2H), 3.44 (s, 3H), 3. 08 (s, 3H), 2.95 (s, 3H), 2.61 (t, J=6. 2 Hz, 2H) ppm. (ES MS M+1= 407. 9)
  • 13
  • [ 192702-01-5 ]
  • [ 865300-49-8 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 12; 6- (3-Chloro-4-fluorobenzyl)-4-hydroxy-N, N, 2-trimethyl-3,5-dioxo-2, 3,5, 6,7, 8-hexahydro-2,6- naphthyridine-1-carboxamide; Step 1 : 1- (3-Chloro-4-fluorobenzyl) piperidin-2-one; Valerolactam (153.3 g, 1.54 mol) was dissolved in NMP (3.5 L) and cooled to 0 C. NaH (67.7g, 1.69 mol, 60% dispersion in oil) was added in portions over 5 minutes keeping the temperature at 0 C. The reaction was stirred for 30 minutes, and 3-chloro-4-fluorobenzylbromide (345.5 g, 1.54 mol) dissolved in 200 mL NMP was added over 30 minutes, again keeping the internal temperature at 0 C. The reaction was aged for 1 hour at 0 C, and allowed to warm to room temperature overnight. LCMS showed the reaction complete. The reaction mixture was quenched with 5L distilled H20, extracted with 3 portions of CH2C12 (2L, 1L, 1L) and the organic layers combined and washed with three 4L portions of water. The organic layer was concentrated and was found to contain NMP. The residual oil was dissolved in EtOAc (4 L), and extracted with three 2L portions of water. The organic layer was concentrated to give the product that solidified upon standing. 1H NMR (400 MHz, CDC13) 8 7.24 (m, 2H), 7.0 (m, 2H), 7.1 (m, 1H), 4.56 (s, 2H), 3.19 (t, J = 4.9, 2H), 2.46 (t, J = 6.4, 2H), 1.8-1. 75 (m, 4H) ppm.
EXAMPLE 23; 6- (3-Chloro-4-fluorobenzyl)-4-hydroxy-N, N, 2-trimethyl-3,5-dioxo-2, 3,5, 6,7, 8-hexahydro-2,6- naphthyridine-1-carboxamide; Step 1: 1- (3-Chloro-4-fluorobenzyl) piperidin-2-one; Valerolactam (60 g) was dissolved in MTBE (1. 5L) at room temperature. To this solution was added Bu4NS04 (4.9 g) as a phase transfer catalyst. The cloudy solution was stirred at room temperature for 5 minutes. Then, NaOH (50 wt%; 300 mL) was slowly added as to keep the internal temperature below 30C. 3-Chloro-4-fluorobenzyl bromide (108.3 g) was then added slowly to this biphasic mixture, again as to keep the internal temperature under control. The reaction was then aged for 4 hours at room temperature. At this time LC showed the reaction to be complete. Water (500 mL) was then added. After phase cut, the organic layer was washed with brine (300 mL), dried under MgS04 followed by solvent switch to heptane (400 mL). The slurry obtained was stirred at room temperature. for 1 hour and then filtered to afford the title product.
To a cold (0 0C) solution of valerolactam (153.30 g, 1.54 mol) in anhydrous l-methyl-2- pyrrolidinone (3.5 L), sodium hydride (67.7 g, 1.69 mol, 60% dispersion in oil) was added over a period of 5 minutes. The reaction mixture was stirred for 30 minutes, and a solution of 3-chloro-4- fluorobenzylbromide (345.5 g, 1.54 mol) in l-methyl-2-pyrrolidinone (200 mL) was added over 30 minutes at 0 0C. The reaction mixture was stirred at 0 0C for 1 hour, and was allowed to warm up and stirred at room temperature overnight. The reaction mixture was quenched with distilled water (5 L), and extracted with dichloromethane (three times; 2 L, 1 L, 1 L). The organic extracts were combined, washed with water (3X; 4 L each time). The residual oil was dissolved in ethyl acetate (4 L), and extracted with water (3X; 2 L each time). The organic layer was separated, concentrated under vacuum to give the title product that solidified upon standing. lHNMR (400 MHz, CDCI3) delta 7.24 (m, 2H), 7.0 (m, 2H), 7.1 (m, IH), 4.56 (s, 2H), 3.19 (t, J= 4.9 Hz,2H), 2.46 (t, J= 6.4 Hz, 2H), 1.8-1.75 (m, 4H).
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; ;