Pyrrolidine → HCID 90229309, compound

HRID 1505791Notes

Reaction equation

[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.C([O:8][C:9](=O)[CH2:10][C:11]1[NH:15][C:14]2[CH:16]=[C:17]([NH:24][C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]([F:36])([F:35])[F:34])=[O:26])[CH:18]=[C:19]([C:20]([O:22][CH3:23])=[O:21])[C:13]=2[N:12]=1)C>C(OCC)(=O)C>[O:8]=[C:9]([N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)[CH2:10][C:11]1[NH:15][C:14]2[CH:16]=[C:17]([NH:24][C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]([F:35])([F:36])[F:34])=[O:26])[CH:18]=[C:19]([C:20]([O:22][CH3:23])=[O:21])[C:13]=2[N:12]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Pyrrolidine (1 mL) was added to methyl 2-(2-ethoxy-2-oxoethyl)-6-({[2-(trifluoromethyl)phenyl]carbonyl}amino)-1H-benzimidazole-4-carboxylate (80 mg), and the solution was stirred at 70° C. for 30 minutes. The reaction mixture was diluted with ethyl acetate, and washed with brine. The ethyl acetate layer was concentrated under reduced pressure. The residue was purified on column chromatography to obtain the titled compound (74 mg) as white powder.

Workup

washwashed with brine
concentrationThe ethyl acetate layer was concentrated under reduced pressure
customThe residue was purified on column chromatography

Sources & evidence

ORD record: ord-1588126fe02442a0b6cf0d73fc82a94e
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216968B2

Reaction notes

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