Hydrochloric Acid → HCID 66588997, compound

HRID 1093196Notes

Reaction equation

[CH:1]12[O:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:9]1[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:34])[NH:23][C:24]4[CH:33]=[CH:32][C:27]([C:28]([O:30]C)=[O:29])=[CH:26][CH:25]=4)=[CH:17][CH:16]=3)[N:12]=[C:11]3[N:35]([CH:38]([CH2:42][O:43][CH3:44])[CH2:39][O:40][CH3:41])[N:36]=[CH:37][C:10]=13)[CH2:2]2.[OH-].[Na+].Cl>O1CCCC1.CO.O>[CH:5]12[O:8][CH:1]([CH2:7][CH2:6]1)[CH2:2][N:3]([C:9]1[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:34])[NH:23][C:24]4[CH:33]=[CH:32][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=4)=[CH:17][CH:16]=3)[N:12]=[C:11]3[N:35]([CH:38]([CH2:42][O:43][CH3:44])[CH2:39][O:40][CH3:41])[N:36]=[CH:37][C:10]=13)[CH2:4]2

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of methyl 4-(3-(4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-(1,3-dimethoxypropan-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl)phenyl)ureido)benzoate (25 mg) in tetrahydrofuran/methanol/water (2:2:1, 20 mL) was treated with two pellets of sodium hydroxide. The mixture was heated overnight at 60° C. and then acidified with concentrated hydrochloric acid to precipitate a fine solid, which, after collection via Buchner filtration, washing with water, and drying under house vacuum, provided 4-(3-(4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-(1,3-dimethoxypropan-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl)phenyl)ureido)benzoic acid. MS (ES+): 588.3 (M+H)+

Workup

customto precipitate a fine solid, which
customafter collection
filtrationvia Buchner filtration
washwashing with water
customdrying under house vacuum

Sources & evidence

ORD record: ord-0882cfd96680428196738447e83c92f4
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129371B2

Reaction notes

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