Hydrochloric Acid → isobutyl ((S)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-yl)methylcarbamate hydrochloride

HRID 2079432Notes

Reaction equation

HRID 2079432 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:17]=[C:16]([N:18]2[CH2:22][CH2:21][C@@H:20]([CH2:23][NH:24][C:25](=[O:31])[O:26][CH2:27][CH:28]([CH3:30])[CH3:29])[CH2:19]2)[C:15]2[C:10](=[CH:11][C:12]([CH3:32])=[CH:13][CH:14]=2)[N:9]=1.[ClH:33].CCOCC>C(Cl)Cl>[ClH:33].[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:17]=[C:16]([N:18]2[CH2:22][CH2:21][C@@H:20]([CH2:23][NH:24][C:25](=[O:31])[O:26][CH2:27][CH:28]([CH3:30])[CH3:29])[CH2:19]2)[C:15]2[C:10](=[CH:11][C:12]([CH3:32])=[CH:13][CH:14]=2)[N:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 136121450isobutyl((S)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-yl)methylcarbamate

Product 1

HCID 136330119isobutyl ((S)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-yl)methylcarbamate hydrochlorideYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of isobutyl ((S)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-yl)methylcarbamate (183 mg, 0.42 mmol) in CH2Cl2 (1.5 mL) was stirred under an N2 atmosphere. A 1.0 M HCl solution in ether (0.42 ml, 0.42 mmol) was added dropwise to this solution. After 10 minutes, 5 mL ether was added, and a precipitate formed which was filtered and dried to obtain isobutyl ((S)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-yl)methylcarbamate hydrochloride (169 mg, 85%). LC/MS: m/z 435.5 (M+H)+at 2.64 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)). 1H NMR (400 MHz, DMSO-d6) δ 8.31 (d, J=8.7 Hz, 1H), 8.24 (d, J=6.8 Hz, 1H), 7.80 (s, 1H), 7.53-7.45 (m, 2H), 7.41-7.38 (m, 1H), 7.12 (d, J=8.2 Hz, 1H), 7.05-7.02 (m, 1H), 4.36-3.85 (m, 5H), 3.77-3.70 (m, 2H), 3.22-3.06 (m, 2H), 2.54 (s, 3H), 2.18-2.13 (m, 1H), 1.87-1.77 (m, 2H), 0.87 (d, J=6.7 Hz, 6H) ppm.

Workup

  1. customa precipitate formed which
  2. filtrationwas filtered
  3. customdried

Sources & evidence

ORD record
ord-64b5663c75e34c1ebd7e3c27a9a7b579
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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