Hydrochloric Acid → (S)-Tetrahydrofuran-3-yl ((R)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-3-yl)methylcarbamate hydrochloride

HRID 2079366Notes

Reaction equation

HRID 2079366 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[CH2:23][CH2:22][CH2:21][C@H:20]([CH2:24][NH:25][C:26](=[O:33])[O:27][C@H:28]3[CH2:32][CH2:31][O:30][CH2:29]3)[CH2:19]2)[C:15]2[C:10](=[CH:11][C:12]([CH3:34])=[CH:13][CH:14]=2)[N:9]=1.[ClH:35].CCOCC>C(Cl)Cl>[ClH:35].[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[CH2:23][CH2:22][CH2:21][C@H:20]([CH2:24][NH:25][C:26](=[O:33])[O:27][C@H:28]3[CH2:32][CH2:31][O:30][CH2:29]3)[CH2:19]2)[C:15]2[C:10](=[CH:11][C:12]([CH3:34])=[CH:13][CH:14]=2)[N:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 136121578(S)-tetrahydrofuran-3-yl ((R)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-3-yl)methylcarbamate

Product 1

HCID 136330117(S)-Tetrahydrofuran-3-yl ((R)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-3-yl)methylcarbamate hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tetrahydrofuran-3-yl ((R)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-3-yl)methylcarbamate in 12 mL CH2Cl2 was added dropwise 2.0 M HCl solution in ether (0.13 mL, 0.25 mmol). To the solution was then added 20 mL ether leading to the precipitation of ((S)-tetrahydrofuran-3-yl ((R)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-3-yl)methylcarbamate hydrochloride which was filtered and dried (116 mg, 92%). LC/MS: m/z 463.5 (M+H)+ at 2.33 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customto the precipitation of ((S)-tetrahydrofuran-3-yl ((R)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-3-yl)methylcarbamate hydrochloride which
  2. filtrationwas filtered
  3. customdried (116 mg, 92%)

Sources & evidence

ORD record
ord-bcf7149e5d9e4210b73414ff8040058c
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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