Sodium Hydroxide → 2-{4-[6-chloro-2-[3-(4-pyridinyl)propyl]-5-(trifluoromethyl)-1H-benzimidazol-1-yl]phenyl}ethanol

HRID 858531Notes

Reaction equation

[Cl:1][C:2]1[C:3]([C:42]([F:45])([F:44])[F:43])=[CH:4][C:5]2[N:9]=[C:8]([CH2:10][CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)[N:7]([C:19]3[CH:24]=[CH:23][C:22]([CH2:25][CH2:26]N(S(C4C=CC(C)=CC=4)(=O)=O)C(=O)[O-])=[CH:21][CH:20]=3)[C:6]=2[CH:41]=1.[OH-:46].[Na+]>C(O)C>[Cl:1][C:2]1[C:3]([C:42]([F:43])([F:44])[F:45])=[CH:4][C:5]2[N:9]=[C:8]([CH2:10][CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)[N:7]([C:19]3[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][OH:46])=[CH:21][CH:20]=3)[C:6]=2[CH:41]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 2-(4-{[5-chloro-2-{[4-(4-pyridinyl)butanoyl]amino}-4-(trifluoromethyl)phenyl]amino}phenyl)ethyl acetate (step 3, 220 mg, 0.42 mmol) and 2N NaOH (15 ml) in ethanol (20 ml) was stirred at 40° C. for 7 h. The solvent was removed and the residue was added water (50 ml). The mixture was extracted with ethyl acetate(100 ml). The organic layer was washed with brine (50 ml), then dried (Na2SO4). After removal of solvent, the crude product was purified by flash column chromatography eluting with dichloromethane:methanol (20:1) to afford 105 mg (54%) of the title compound as pale brown oil.

Workup

customThe solvent was removed
additionthe residue was added water (50 ml)
extractionThe mixture was extracted with ethyl acetate(100 ml)
washThe organic layer was washed with brine (50 ml)
dry with materialdried (Na2SO4)
customAfter removal of solvent
customthe crude product was purified by flash column chromatography
washeluting with dichloromethane:methanol (20:1)

Sources & evidence

ORD record: ord-407e7ee4cc3a451d9de554bc43508324
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148234B2

Reaction notes

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