Hydrochloric Acid → HCID 136330118, compound

HRID 2079387Notes

Reaction equation

HRID 2079387 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[C:9]1[N:18]=[C:17]([N:19]2[CH2:24][CH2:23][CH2:22][C@@H:21]([CH2:25][NH:26][C:27](=[O:31])[O:28][CH2:29][CH3:30])[CH2:20]2)[C:16]2[C:11](=[CH:12][C:13]([CH3:32])=[CH:14][CH:15]=2)[N:10]=1.CCOCC.[ClH:38]>C(Cl)Cl>[ClH:38].[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[C:9]1[N:18]=[C:17]([N:19]2[CH2:24][CH2:23][CH2:22][C@@H:21]([CH2:25][NH:26][C:27](=[O:31])[O:28][CH2:29][CH3:30])[CH2:20]2)[C:16]2[C:11](=[CH:12][C:13]([CH3:32])=[CH:14][CH:15]=2)[N:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 136121330HCID 136121330, compound

Product 1

HCID 136330118HCID 136330118, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl ((S)-1-(2-(2-fluoro-6-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-3-yl)methylcarbamate (89 mg, 0.2 mmol) in 2 mL CH2Cl2 under an N2 atmosphere was added ether (10 mL) followed by the dropwise addition of a 2.0 M solution of HCl in ether (0.1 mL, 0.2 mmol) which resulted in precipitation of ethyl ((S)-1-(2-(2-fluoro-6-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-3-yl)methylcarbamate hydrochloride which was then filtered and dried (85 mg, 90%). LC/MS: m/z 439.5 (M+H)+ at 2.37 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)). 1H NMR (400 MHz, DMSO-d6) δ 8.26 (d, J=8.5 Hz, 1H), 7.57 (s, 1H), 7.45 (m, 2H), 6.81 (m, 2H), 4.57 (m, 2H), 3.89 (m, 2H), 3.52 (m, 1H), 3.36 (m, 1H), 2.95 (s, 2H), 2.52 (s, 3H), 1.86 (m, 3H), 1.66 (m, 1H), 1.39 (m, 1H), 1.07 (t, J=6.6 Hz, 3H) ppm.

Sources & evidence

ORD record
ord-6354930fb1744f4a81ba1845a0751a65
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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