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

HRID 2079434Notes

Reaction equation

HRID 2079434 reaction equation
[ClH:1].CCOCC.[OH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[N:23]=[C:22]([N:24]2[CH2:28][CH2:27][C@@H:26]([CH2:29][NH:30][C:31](=[O:37])[O:32][CH2:33][CH2:34][O:35][CH3:36])[CH2:25]2)[C:21]2[C:16](=[CH:17][C:18]([CH3:38])=[CH:19][CH:20]=2)[N:15]=1>C(Cl)Cl>[ClH:1].[OH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[N:23]=[C:22]([N:24]2[CH2:28][CH2:27][C@@H:26]([CH2:29][NH:30][C:31](=[O:37])[O:32][CH2:33][CH2:34][O:35][CH3:36])[CH2:25]2)[C:21]2[C:16](=[CH:17][C:18]([CH3:38])=[CH:19][CH:20]=2)[N:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 1361215232-methoxyethyl((S)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-yl)methylcarbamate

Product 1

HCID 1363301202-methoxyethyl ((S)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-yl)methylcarbamate hydrochlorideYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 1.0 M HCl solution in Et2O (0.27 mL, 0.27 mmol) was slowly added to a stirring solution of 2-methoxyethyl ((S)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-yl)methylcarbamate (0.12 g, 0.27 mmol) in CH2Cl2 (5 mL). The reaction was stirred for 30 minutes at room temperature, then Et2O was slowly added to the solution until a precipitate formed. After stirring for 1 h, the solid was filtered and washed with Et2O to obtain 2-methoxyethyl ((S)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-yl)methylcarbamate hydrochloride (0.10 g, 77%). LC/MS: m/z 437.1 (M+H)+ at 2.19 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customformed
  2. stirringAfter stirring for 1 h
  3. filtrationthe solid was filtered
  4. washwashed with Et2O

Sources & evidence

ORD record
ord-9824a1571a144cd1aff7283df0e354de
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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