Potassium Hydroxide → 2-{3-[7-(4-Fluoro-phenyl)-4-oxo-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl]-phenyl}-thiazole-4-carboxylic acid

HRID 1062250Notes

Reaction equation

C([O:3][C:4]([C:6]1[N:7]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]3[CH2:18][C:19](=[O:35])[NH:20][C:21]4[CH:27]=[C:26]([C:28]5[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=5)[CH:25]=[CH:24][C:22]=4[N:23]=3)[CH:12]=2)[S:9][CH:10]=1)=[O:5])C.[OH-].[K+]>CO.CS(C)=O>[F:34][C:31]1[CH:32]=[CH:33][C:28]([C:26]2[CH:25]=[CH:24][C:22]3[N:23]=[C:17]([C:13]4[CH:12]=[C:11]([C:8]5[S:9][CH:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]=5)[CH:16]=[CH:15][CH:14]=4)[CH2:18][C:19](=[O:35])[NH:20][C:21]=3[CH:27]=2)=[CH:29][CH:30]=1

Participants

Conditions

Temperature: 23 °C

Procedure

To a solution of 2-{3-[7-(4-fluoro-phenyl)-4-oxo-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl]-phenyl}-thiazole-4-carboxylic acid ethyl ester (Example 153) (49 mg, 0.1 mmol) in a mixture of MeOH (1 mL) and DMSO (1.5 mL) was added 2N KOH (1 mL, 2 mmol). The mixture was stirred at 23° C. for 0.5 h and then partitioned between ethyl acetate and H2O. The pH of the aqueous phase was set to 3 by the addition of 3N HCl and then stirred in the ice-bath for 0.5 h. The precipitate was collected by filtration, triturated with EtOH/Et2O (1/1) and dried, to give the title compound as light yellow solid (25 mg).

Workup

custompartitioned between ethyl acetate and H2O
additionThe pH of the aqueous phase was set to 3 by the addition of 3N HCl
stirringstirred in the ice-bath for 0.5 h
filtrationThe precipitate was collected by filtration
customtriturated with EtOH/Et2O (1/1)
customdried

Sources & evidence

ORD record: ord-e1064f2fe1994d939386f1d14d0af204
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06960578B2

Reaction notes

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