Formaldehyde → HCID 71532469, compound

HRID 1505783Notes

Reaction equation

HRID 1505783 reaction equation
Cl.Cl.[Cl:3][C:4]1[C:5]([CH3:40])=[C:6]([NH:10][C:11]([C:13]2[C:21]3[N:20]=[C:19]([C@@H:22]4[CH2:26][CH2:25][CH2:24][NH:23]4)[NH:18][C:17]=3[CH:16]=[C:15]([NH:27][C:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[C:36]([F:39])([F:38])[F:37])=[O:29])[CH:14]=2)=[O:12])[CH:7]=[CH:8][CH:9]=1.C=O.B.N1C=CC=C[C:45]=1C>CO>[Cl:3][C:4]1[C:5]([CH3:40])=[C:6]([NH:10][C:11]([C:13]2[C:21]3[N:20]=[C:19]([C@@H:22]4[CH2:26][CH2:25][CH2:24][N:23]4[CH3:45])[NH:18][C:17]=3[CH:16]=[C:15]([NH:27][C:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[C:36]([F:39])([F:37])[F:38])=[O:29])[CH:14]=2)=[O:12])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 16217944Borane;2-methylpyridineHCID 90229289HCID 90229289, compound

Product 1

HCID 71532469HCID 71532469, compoundYield 48.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(3-chloro-2-methylphenyl)-2-[(2S)-pyrrolidin-2-yl]-6-({[2-(trifluoromethyl)phenyl]carbonyl}amino)-1H-benzimidazole-4-carboxamide (Example 71) (25 mg) in MeOH (0.4 mL), was added 38% aqueous formaldehyde solution (7.2 μL), and the mixture was stirred at room temperature overnight. To the mixture was added 2-picoline borane (10 mg), it was stirred for 3 hours, and the solvent was removed under reduced pressure. The residue was purified on column chromatography to obtain the titled compound (11 mg) as white powder.

Workup

  1. stirringwas stirred for 3 hours
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was purified on column chromatography

Sources & evidence

ORD record
ord-db6d0275d3854e638b0eebe5fda0f6a4
Source dataset
uspto-grants-2015_12
Patent number
US09216968B2

Reaction notes

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