Hydrochloric Acid → (R)-ethyl 1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate hydrochloride

HRID 1693011Notes

Reaction equation

HRID 1693011 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]([NH:29][C:30](=[O:34])[O:31][CH2:32][CH3:33])[CH2:25]2)[C:21]2[C:16](=[CH:17][C:18]([CH3:35])=[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]([NH:29][C:30](=[O:34])[O:31][CH2:32][CH3:33])[CH2:25]2)[C:21]2[C:16](=[CH:17][C:18]([CH3:35])=[CH:19][CH:20]=2)[N:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 135410876(R)-ethyl 1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate

Product 1

HCID 136406831(R)-ethyl 1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under an N2 atmosphere, a 1.0 M solution of HCl in ether (0.53 mL, 0.53 mmol) was added dropwise to a solution of (R)-ethyl 1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate (208 mg, 0.53 mmol) in CH2Cl2 (13 mL). After stirring the reaction for 10 minutes, ether (30 mL) was added, and a precipitate formed which was filtered and dried to give (R)-ethyl 1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate hydrochloride (HCl salt of compound 2). 1H NMR (400 MHz, DMSO-d6) δ 8.29-8.23 (m, 2H), 7.78 (s, 1H), 7.61 (d, J=5.1 Hz, 1H), 7.52-7.48 (m, 2H), 7.10 (d, J=8.1 Hz, 1H), 7.06-7.02 (m, 2H), 4.29-4.13 (m, 4H), 4.03-3.94 (m, 3H), 2.54 (s, 3H), 2.27-2.22 (m, 1H), 2.08-2.06 (m, 1H), 1.16 (t, J=7.0 Hz, 3H) ppm. LC/MS: m/z 393.3 (M+H)+ at 2.36 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customthe reaction for 10 minutes
  2. customa precipitate formed which
  3. filtrationwas filtered
  4. customdried

Sources & evidence

ORD record
ord-a62c1b7eee45498081a6c78292d7d624
Source dataset
uspto-grants-2012_04
Patent number
US08158637B2

Reaction notes

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