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

HRID 1693021Notes

Reaction equation

HRID 1693021 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]([NH:23][C:24](=[O:30])[O:25][CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:19]2)[C:15]2[C:10](=[CH:11][C:12]([CH3:31])=[CH:13][CH:14]=2)[N:9]=1.[ClH:32]>CCOCC>[ClH:32].[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]([NH:23][C:24](=[O:30])[O:25][CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:19]2)[C:15]2[C:10](=[CH:11][C:12]([CH3:31])=[CH:13][CH:14]=2)[N:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 135771831(R)-isobutyl 1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate

Product 1

HCID 136400608(R)-isobutyl 1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate hydrochlorideYield 90%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Under an N2 atmosphere, anhydrous ether (12 mL) was added to a solution of (R)-isobutyl 1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate (306 mg, 0.73 mmol). A 2.0 M HCl solution in ether (0.365 mL, 0.73 mmol) was added over a period of 45 seconds, upon which a precipitate formed. The reaction was stirred for 10 additional minutes, before the solid was obtained by vacuum filtration and dried under high vacuum to give (R)-isobutyl 1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate hydrochloride (HCl salt of compound 5) (300 mg, 90%). 1H NMR (400 MHz, acetic acid-d4) δ 8.28 (d, J=8.3 Hz, 1H), 8.20 (m, 1H), 7.75 (s, 1H), 7.53 (m, 2H), 7.08 (m, 2H), 4.00 (m, 7H), 2.54 (s, 3H), 2.27 (m, 1H), 2.01 (m, 1H), 1.82 (m, 1H), 0.87 (d, J=6.5 Hz, 6H) ppm. LC/MS: m/z 421.0 (M+H)+ at 2.54 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customformed
  2. customwas obtained by vacuum filtration
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-166273204efa4e32bda1392a0059a8c9
Source dataset
uspto-grants-2012_04
Patent number
US08158637B2

Reaction notes

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