3-Chloro-4-methylaniline → HCID 71267522, compound

HRID 1505811Notes

Reaction equation

HRID 1505811 reaction equation
[CH3:1][N:2]([CH3:28])[C:3]1[NH:7][C:6]2[CH:8]=[C:9]([NH:15][C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]([F:27])([F:26])[F:25])=[O:17])[CH:10]=[C:11]([C:12]([OH:14])=O)[C:5]=2[N:4]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[Cl:62][C:63]1[CH:64]=[C:65]([CH:67]=[CH:68][C:69]=1[CH3:70])[NH2:66]>CN(C=O)C.C(OCC)(=O)C>[Cl:62][C:63]1[CH:64]=[C:65]([NH:66][C:12]([C:11]2[C:5]3[N:4]=[C:3]([N:2]([CH3:28])[CH3:1])[NH:7][C:6]=3[CH:8]=[C:9]([NH:15][C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]([F:25])([F:26])[F:27])=[O:17])[CH:10]=2)=[O:14])[CH:67]=[CH:68][C:69]=1[CH3:70]

Participants

7

Reactant 4

HCID 72553-Chloro-4-methylanilineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 90229321HCID 90229321, compound

Product 1

HCID 71267522HCID 71267522, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(dimethylamino)-6-({[2-(trifluoromethyl)phenyl]carbonyl}amino)-1H-benzimidazole-4-carboxylic acid (50 mg) and HATU (82 mg) in DMF (1 mL), were added N,N-diisopropylethylamine (88 μL) and 3-chloro-4-methylaniline (26 μL), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate, washed sequentially with saturated aqueous sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified on column chromatography to obtain N-(3-chloro-4-methylphenyl)-2-(dimethylamino)-6-({[2-(trifluoromethyl)phenyl]carbonyl}amino)-1H-benzimidazole-4-carboxamide (65 mg) as white powder. This was suspended in MeOH (1.5 mL), 2N hydrogen chloride/MeOH (1 Eq) was added, and it was stirred and concentrated. The residue was triturated in diethyl ether, and the precipitate was collected by filtration and dried to obtain the titled compound (40 mg) as white powder.

Workup

  1. washwashed sequentially with saturated aqueous sodium bicarbonate and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified on column chromatography

Sources & evidence

ORD record
ord-9e6725ae75d34193b4eff494a3d08ac9
Source dataset
uspto-grants-2015_12
Patent number
US09216968B2

Reaction notes

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