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Chemical Structure| 101385-93-7 Chemical Structure| 101385-93-7
Chemical Structure| 101385-93-7

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Product Details of [ 101385-93-7 ]

CAS No. :101385-93-7
Formula : C9H15NO3
M.W : 185.22
SMILES Code : O=C(N1CC(CC1)=O)OC(C)(C)C
MDL No. :MFCD01631194
InChI Key :JSOMVCDXPUXKIC-UHFFFAOYSA-N
Pubchem ID :471360

Safety of [ 101385-93-7 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H315-H318-H335
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312+P330-P302+P352-P304+P340+P312-P305+P351+P338+P310-P332+P313-P403+P233-P405-P501

Calculated chemistry of [ 101385-93-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 13
Num. arom. heavy atoms 0
Fraction Csp3 0.78
Num. rotatable bonds 3
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 51.99
TPSA ?

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

46.61 ?2

Lipophilicity

Log Po/w (iLOGP)?

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

2.18
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

0.66
Log Po/w (WLOGP)?

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

0.82
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.

0.45
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

0.86
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.99

Water Solubility

Log S (ESOL):?

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

-1.21
Solubility 11.5 mg/ml ; 0.0622 mol/l
Class?

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

Very soluble
Log S (Ali)?

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

-1.21
Solubility 11.3 mg/ml ; 0.061 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

-1.11
Solubility 14.2 mg/ml ; 0.0767 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

 No
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.

-6.96 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)

 1.96

Application In Synthesis of [ 101385-93-7 ]

* 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.

  • Upstream synthesis route of [ 101385-93-7 ]
  • Downstream synthetic route of [ 101385-93-7 ]

[ 101385-93-7 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 101385-93-7 ]
  • [ 3760-52-9 ]
References: [1] Patent: US2009/29963, 2009, A1, . Location in patent: Page/Page column 14.
[2] Chemistry - A European Journal, 2018, vol. 24, # 55, p. 14836 - 14843.
  • 2
  • [ 101385-93-7 ]
  • [ 365996-87-8 ]
References: [1] Patent: WO2006/127530, 2006, A2, .
  • 3
  • [ 81290-20-2 ]
  • [ 101385-93-7 ]
  • [ 644970-36-5 ]
References: [1] Patent: WO2004/5295, 2004, A1, . Location in patent: Page 158-159.
[2] Patent: EP2540728, 2013, A1, . Location in patent: Page/Page column 76.
  • 4
  • [ 75-16-1 ]
  • [ 101385-93-7 ]
  • [ 412278-02-5 ]
YieldReaction ConditionsOperation in experiment
92% at 20℃; for 1 h; Inert atmosphere To an ice-cold solution of tert-butyl 3-oxopyrrolidine-1-carboxylate (1.0 g, 5.40 mmol) in Et2O (20 mL) was added methylmagnesium bromide (3.50 mL, 10.80 mmol.) drop wise under an inert atmosphere.
The mixture was stirred at RT for 1 h, then quenched with NH4Cl solution followed by extraction with EtOAc (3*100 mL).
The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo.
Trituration with n-pentane gave i (1.0 g, 92percent).
3-Methylpyrrolidin-3-ol hydrochloride (Precursor 52): To a solution of 4M HCl in 1,4-dioxane (10 mL) at 0° C. was added i (0.850 g, 4.22 mmol) and the mixture stirred for 2 h at RT.
83.8%
Stage #1: With lithium chloride; zinc(II) chloride In tetrahydrofuran; diethyl ether at -10℃; for 1 h;
Stage #2: for 0.5 h; 		(2)
Preparation of tert-butyl 3-hydroxy-3-methylpyrrolidine-1-carboxylate
To a 30 L reaction kettle was added 4 L dry THF at -10° C.
After stirring, to the mixture were added ZnCl2 (118 g, 0.86 mol) and LiCl (402 g, 9.5 mol).
After half an hour, to the resulting mixture was slowly added a solution of MeMgBr (3 mol/L) in diethyl ether (6.4 L, 19.2 mol) dropwisely.
The stirring was continued for half an hour.
To the resulting mixture was slowly added a solution of tert-butyl 3-oxopyrrolidine-1-carboxylate (1600 g, 8.6 mol) in THF dropwisely.
After the completion of reaction by HPLC detection, to the system was dropwisely added a saturated NH4Cl solution to quench off the reaction.
The reaction was extracted with ethyl acetate.
The organic phase was washed with a saturated aqueous NaCl solution, dried over anhydrous sodium sulfate, and evaporated to remove the solvent to produce tert-butyl 3-hydroxy-3-methylpyrrolidine-1-carboxylate as a pale yellow solid (1450 g) in a yield of 83.8percent.
83.8% With lithium chloride; zinc(II) chloride In tetrahydrofuran; diethyl ether (2)
Preparation of tert-butyl 3-hydroxy-3-methylpyrrolidine -1-carboxylate
To a 30 L reaction kettle was added 4 L dry THF at -10°C.
After stirring, to the mixture were added ZnCl2 (118g, 0.86mol) and LiCl (402g, 9.5mol).
After half an hour, to the resulting mixture was slowly added a solution of MeMgBr (3mol/L) in diethyl ether (6.4 L, 19.2mol) dropwisely.
The stirring was continued for half an hour.
To the resulting mixture was slowly added a solution of tert-butyl 3-oxopyrrolidine-1-carboxylate (1600g, 8.6mol) in THF dropwisely.
After the completion of reaction by HPLC detection, to the system was dropwisely added a saturated NH4Cl solution to quench off the reaction.
The reaction was extracted with ethyl acetate.
The organic phase was washed with a saturated aqueous NaCl solution, dried over anhydrous sodium sulfate, and evaporated to remove the solvent to produce tert-butyl 3-hydroxy-3-methylpyrrolidine-1-carboxylate as a pale yellow solid (1450 g) in a yield of 83.8 percent.
83.8% With lithium chloride; zinc(II) chloride In tetrahydrofuran; diethyl ether at -10℃; for 0.5 h; (2)
Preparation of tert-butyl 3-hydroxy-3-methylpyrrolidine -1-carboxylate
To a 30 L reaction kettle was added 4 L dry THF at -10°C.
After stirring, to the mixture were added ZnCl2 (118g, 0.86mol) and LiCl (402g, 9.5mol).
After half an hour, to the resulting mixture was slowly added dropwisely a solution of MeMgBr (3mol/L) in diethyl ether (6.4 L, 19.2mol).
The stirring was continued for half an hour.
To the resulting mixture was slowly added a solution of tert-butyl 3-oxopyrrolidine -1-carboxylate (1600g, 8.6mol) in THF dropwisely.
After the completion of reaction by HPLC detection, to the system was dropwisely added a saturated NH4Cl solution to quench off the reaction.
The reaction was extracted with ethyl acetate.
The organic phase was washed with a saturated aqueous NaCl solution, dried over anhydrous sodium sulfate, and evaporated to remove the solvent to produce tert-butyl 3-hydroxy-3-methylpyrrolidine-1-carboxylate as a pale-yellow solid (1450g) in a yield of 83.8 percent.
70% at -78℃; for 4 h; The solution of (0.070 g, 0.38 mmol) tert-butyl 3-oxopyrrolidine-l- carboxylate in anhydrous THF (2 mL) was cooled to -78°C. Then the solution of 1 M methylmagnesium bromide in butyl ether was added dropwise. The reaction was stirred at - 78°C for 4 h and quenched by water (2 mL). After concentrating the reaction in vacuo, the residue was partitioned between ethyl acetate and water. The aqueous layer was extracted once more with ethyl acetate, and the combined organic layers were washed with brine, dried (MgSO4) and concentrated. The residue was purified by silica flash chromatography (gradient elution, using 1 : 1 hexane-ethyl acetate and ethyl acetate) to provide the title compound (0.054 g, 70percent).
69% at 0 - 20℃; for 1 h; EXAMPLE 310 Synthesis of rac-4-((1-benzyl-3-methylpyrrolidin-3-yl)oxy)-5-chloro-2-fluoro-/\/-(thiazol-4-yl)benzenesulfonamide Step 1. Preparation of rac-te/f-butyl 3-hydroxy-3-methylpyrrolidine-1-carboxylate To a cooled (0 °C) solution of te/f-butyl 3-oxopyrrolidine-1-carboxylate (0.975 g, 5.26 mmol) in anhydrous diethyl ether (20 mL)) was added a 3 M solution of methylmagnesium bromide in diethyl ether (3.50 mL, 10.53 mmol). The reaction was allowed to warm to ambient temperature, stirred for 1 hour, and then cooled to 0 °C and quenched by addition of saturated aqueous ammonium chloride (15 mL). The aqueous layer was separated and extracted with ethyl acetate (3 χ 100 mL). The combined organic phases were washed with brine (50 mL), dried with magnesium sulfate, and filtered. Concentration of the filtrate in vacuo and purification of the residue by column chromatography, eluting with a gradient of 0-40percent of ethyl acetate in hexanes, provided the title compound as a yellowish oil (0.735 g, 69percent yield) H NMR (300 MHz, CDCIs) 3.54-3.44 (m, 2H), 3.42-3.33 (m, 1 H), 3.28-3.20 (m, 1 H), 1.93-1.79 (m, 2H), 1.60-1.56 (m, 1 H), 1.46 (s, 9H), 1.42 (s, 3H); MS (ES+) m/z 202.3 (M + 1).
105 mg at 0 - 20℃; for 1 h; 3.0 M ether solution of methylmagnesium bromide (540 .il, 1.62 mmol) wasadded to a solution of tert-butyl 3-oxopyrrolidine-1-carboxylate (100 mg, 0.540 mmol) in THF (2 ml) at 0 °C and warmed up to rt for 1 hr., quenched with saturated NH4C1 (2 ml), extracted with ethyl acetate (60 ml), washed with water, brine, dried (MgSO4) andconcentrated under reduced pressure to provide tert-butyl 3 -hydroxy-3 -methylpyrrolidine1-carboxylate (105 mg) which was used as such for the next step without purification. ‘H NMR (400MHz, CDC13) ? ppm 3.60 - 3.18 (m, 4H), 1.97 - 1.80 (m, 2H), 1.56 - 1.38 (m, 12H).

References: [1] Patent: US2013/252938, 2013, A1, . Location in patent: Paragraph 0514.
[2] Patent: US2014/45896, 2014, A1, . Location in patent: Paragraph 0134; 0135; 0199; 0200.
[3] Patent: EP2703398, 2014, A1, . Location in patent: Paragraph 0119; 0120.
[4] Patent: EP2703398, 2014, A1, . Location in patent: Paragraph 0173; 0174.
[5] Journal of the American Chemical Society, 2015, vol. 137, # 35, p. 11270 - 11273.
[6] Patent: WO2008/24725, 2008, A1, . Location in patent: Page/Page column 123.
[7] Patent: WO2017/201468, 2017, A1, . Location in patent: Page/Page column 420-421.
[8] Patent: WO2015/35278, 2015, A1, . Location in patent: Page/Page column 87.
  • 5
  • [ 101385-93-7 ]
  • [ 74-88-4 ]
  • [ 412278-02-5 ]
YieldReaction ConditionsOperation in experiment
64% With iodine; magnesium In diethyl ether at 0 - 20℃; for 1.5 h; Inert atmosphere To a stirred suspension of magnesium (2.59 g, 106 mmol, 1.97 equiv) in 50 mL of dry ether were added iodine (catalytic) and methyl iodide (6.7 mL, 108 mmol, 2 equiv) slowly drop wise at 0°C under argon atmosphere. This was added to a solution of tert-butyl 3- oxopyrrolidine-1-carboxylate (10 g, 54 mmol, 1 equiv) in 50 mL of ether at 0°C. The reaction mixture was warmed to room temperature and stirred for 1.5 h. After completion, the reactionwas quenched with saturated ammonium chloride solution at 0 °C and extracted with EtOAc. The combined organic extract was dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification using silica gel column chromatography (20percent EtOAc hexanes) afforded 7.0 g of tert-butyl 3-hydroxy-3-methylpyrrolidine-1-carboxylate (Yield = 64percent).
48%
Stage #1: With magnesium In diethyl ether
Stage #2: at 0 - 20℃; for 1.5 h;
Stage #3: With water; ammonium chloride In diethyl ether at 0℃; 		c) tert-Bntyl S-hydroxy-S-methylpyrrolidine-l-carboxylate; Methyl magnesium iodide [prepared from magnesium metal (1.73 g, 0.071 mol) and methyl iodide (4.7 mL, 0.074 mol) in dry ether (50 mL)] was slowly added to the solution of step b) product (6.6 g, 0.036 mol) in dry ether (150 mL) at 0 0C under nitrogen atm. The reaction mixture was slowly warmed to RT and stirred for 1.5 h and after cooling to 0 0C, it was quenched with saturated NH4Cl solution. The two layers were separated and the aqueous layer was extracted with ethyl acetate (3xl00mL). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The crude product was purified by column chromatography using 40 percent EtOAc in pet. ether. Yield =3.4 g (48 percent). The product was used directly in step d).
References: [1] Patent: WO2016/100940, 2016, A1, . Location in patent: Page/Page column 151.
[2] Patent: WO2007/11284, 2007, A1, . Location in patent: Page/Page column 29.
  • 6
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  • [ 101385-93-7 ]
  • [ 412278-02-5 ]
References: [1] Patent: US2014/45896, 2014, A1, . Location in patent: Paragraph 0081; 0082.
 

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