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

HRID 2406191Notes

Reaction equation

HRID 2406191 reaction equation
CCOCC.[OH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[N:22]=[C:21]([N:23]2[CH2:27][CH2:26][C@@H:25]([NH:28][C:29](=[O:35])[O:30][CH2:31][CH2:32][O:33][CH3:34])[CH2:24]2)[C:20]2[C:15](=[CH:16][C:17]([CH3:36])=[CH:18][CH:19]=2)[N:14]=1.[ClH:37]>C(Cl)Cl>[ClH:37].[OH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[N:22]=[C:21]([N:23]2[CH2:27][CH2:26][C@@H:25]([NH:28][C:29](=[O:35])[O:30][CH2:31][CH2:32][O:33][CH3:34])[CH2:24]2)[C:20]2[C:15](=[CH:16][C:17]([CH3:36])=[CH:18][CH:19]=2)[N:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether3×HCID 135771844(R)-2-methoxyethyl 1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate

Product 1

HCID 136397157(R)-2-methoxyethyl 1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate hydrochlorideYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under an N2 atmosphere, ether (5 mL) was added to a solution of (R)-2-methoxyethyl 1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate (200 mg, 0.47 mmol) in CH2Cl2 (1 mL). A 2.0 M HCl solution in ether (0.236 mL, 0.47 mmol) was added, upon which a precipitate formed. Additional ether was added (5 mL), and the mixture was stirred for 30 minutes. The solid was filtered and dried under vacuum to obtain (R)-2-methoxyethyl 1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate hydrochloride (HCl salt of compound 14) (160 mg, 80%). 1H NMR (400 MHz, DMSO-d6) δ 8.29-8.24 (m, 2H), 7.82 (s, 1H), 7.75 (d, J=5.5 Hz, 1H), 7.53-7.49 (m, 2H), 7.14 (d, J=8.2 Hz, 1H), 7.06-7.02 (m, 1H), 4.29-3.95 (m, 7H, water in this region), 3.50-3.47 (m, 2H), 3.23 (s, 3H), 2.54 (s, 3H), 2.26-2.23 (m, 1H), 2.08-2.07 (m, 1H) ppm. LC/MS: m/z 423.3 (M+H)+ at 2.22 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customformed
  2. filtrationThe solid was filtered
  3. customdried under vacuum

Sources & evidence

ORD record
ord-adf85f8047654253b5faa2fd28ee966e
Source dataset
uspto-grants-2014_08
Patent number
US08809353B2

Reaction notes

Loading…