Hydrochloric Acid → HCID 178461550, compound

HRID 912976Notes

Reaction equation

C[O:2][C:3](=[O:40])[C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[NH:21][C:20]4[CH:22]=[C:23]([C:35]([F:38])([F:37])[F:36])[CH:24]=[C:25]([C:26]5[CH:31]=[C:30]([F:32])[C:29]([F:33])=[C:28]([F:34])[CH:27]=5)[C:19]=4[N:18]=3)[C@H:13]([CH3:39])[CH2:12]2)=[N:6][CH:5]=1.[OH-].[Na+].Cl>C1COCC1>[Cl:10][C:8]1[C:7]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[NH:18][C:19]4[C:25]([C:26]5[CH:31]=[C:30]([F:32])[C:29]([F:33])=[C:28]([F:34])[CH:27]=5)=[CH:24][C:23]([C:35]([F:38])([F:36])[F:37])=[CH:22][C:20]=4[N:21]=3)[C@H:13]([CH3:39])[CH2:12]2)=[N:6][CH:5]=[C:4]([CH:9]=1)[C:3]([OH:40])=[O:2]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 5-chloro-6-{(3R)-3-methyl-4-[6-trifluoromethyl-4-(3,4,5-trifluoro-phenyl)-1H-benzoimidazol-2-yl]-piperazin-1-yl}-nicotinic acid methyl ester (58 mg, 0.1 mmol, Example 178c) and 1N NaOH (0.11 mL) in THF (1 mL) was stirred at 50° C. for 16 h. 1N HCl (0.11 mL) was added and the mixture was extracted with EtOAc (2×20 mL). The combined organic extracts were washed with brine (5 mL), dried over Na2SO4 and filtered. The filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography, eluting with 10% MeOH/EtOAc to give the title compound as a white amorphous solid. MS (ESI, pos. ion) m/e: 570 (M+1).

Workup

extractionthe mixture was extracted with EtOAc (2×20 mL)
washThe combined organic extracts were washed with brine (5 mL)
dry with materialdried over Na2SO4
filtrationfiltered
customThe filtrate was evaporated in vacuo
customthe residue was purified by silica gel column chromatography
washeluting with 10% MeOH/EtOAc

Sources & evidence

ORD record: ord-06b73f4c529f4f5e8ff6aa8ec1bf2599
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026241B2

Reaction notes

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