Hydrochloric Acid → 3-Bromo-4-{[(4-tert-butylcyclohexyl)(5-methoxy-1-methyl-1h-benzimidazol-2-yl)amino]methyl}benzoic acid

HRID 230017Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH2:12][N:13]([CH:26]1[CH2:31][CH2:30][CH:29]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:28][CH2:27]1)[C:14]1[N:18]([CH3:19])[C:17]2[CH:20]=[CH:21][C:22]([O:24][CH3:25])=[CH:23][C:16]=2[N:15]=1)[C:5]([O:7]C)=[O:6].[Li+].[OH-].CCOC(C)=O.Cl>O1CCOCC1.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH2:12][N:13]([CH:26]1[CH2:27][CH2:28][CH:29]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:30][CH2:31]1)[C:14]1[N:18]([CH3:19])[C:17]2[CH:20]=[CH:21][C:22]([O:24][CH3:25])=[CH:23][C:16]=2[N:15]=1)[C:5]([OH:7])=[O:6]

Participants

Conditions

Temperature: 40 °C

Procedure

To the title compound of Example 224 Step D (0.07 mmol, 40 mg) in 2 mL of dioxane was added a solution of LiOH (1 mmol, 24 mg) in 1 mL of H2O. The reaction was allowed to stir at 40° C. for 1.5 h. The crude reaction mixture was poured into pH 7 buffer/EtOAc, which was acidified with 2 N HCl until two clear layers formed after agitation. The organic phase was collected and the aqueous phase was extracted twice with EtOAc. The combined organic phase was dried over Na2SO4, then concentrated under reduced pressure to afford the product as a slightly yellow-green foam. HPLC A: 2.32 min.

Workup

customThe crude reaction mixture
customformed after agitation
customThe organic phase was collected
extractionthe aqueous phase was extracted twice with EtOAc
dry with materialThe combined organic phase was dried over Na2SO4
concentrationconcentrated under reduced pressure
customto afford the product as a slightly yellow-green foam
custom2.32 min.

Sources & evidence

ORD record: ord-4776b4418b33418490a2decccacea137
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07563815B2

Reaction notes

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