Hydrochloric Acid → HCID 136366890, compound

HRID 2062302Notes

Reaction equation

HRID 2062302 reaction equation
C([O:3][C:4](=[O:32])[NH:5][CH2:6][C@@H:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]2[C:22]3[C:17](=[CH:18][C:19]([CH3:23])=[CH:20][CH:21]=3)[N:16]=[C:15]([C:24]3[C:29]([OH:30])=[CH:28][CH:27]=[CH:26][C:25]=3[F:31])[N:14]=2)[CH2:8]1)C.[CH3:33][CH2:34]OCC.[ClH:38]>C(Cl)Cl>[ClH:38].[CH2:33]([N:5]([CH2:6][C@H:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]2[C:22]3[C:17](=[CH:18][C:19]([CH3:23])=[CH:20][CH:21]=3)[N:16]=[C:15]([C:24]3[C:29]([OH:30])=[CH:28][CH:27]=[CH:26][C:25]=3[F:31])[N:14]=2)[CH2:8]1)[C:4](=[O:32])[OH:3])[CH3:34]

Participants

5

Reactant 3

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

Product 1

HCID 136366890HCID 136366890, 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).

Sources & evidence

ORD record
ord-8de7d29665fd4e21931d4f85c3d72e60
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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