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3-Chloro-2-methylaniline → Friluglanstat

HRID 1505771
Notes
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Reaction equation

HRID 1505771 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[NH:8][C:7]2[CH:9]=[C:10]([NH:16][C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]([F:28])([F:27])[F:26])=[O:18])[CH:11]=[C:12]([C:13]([OH:15])=O)[C:6]=2[N:5]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl:53][C:54]1[C:55]([CH3:61])=[C:56]([CH:58]=[CH:59][CH:60]=1)[NH2:57].C(=O)(O)[O-].[Na+]>CN(C=O)C.C(N(CC)CC)C>[Cl:53][C:54]1[C:55]([CH3:61])=[C:56]([NH:57][C:13]([C:12]2[C:6]3[N:5]=[C:4]([CH2:3][O:2][CH3:1])[NH:8][C:7]=3[CH:9]=[C:10]([NH:16][C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]([F:26])([F:28])[F:27])=[O:18])[CH:11]=2)=[O:15])[CH:58]=[CH:59][CH:60]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 68943-Chloro-2-methylanilineHCID 516892Sodium BicarbonateHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 90229242HCID 90229242, compound

Product 1

HCID 71267445Friluglanstat

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent
HCID 8471TriethylamineSolvent

Procedure

To a solution of 2-(methoxymethyl)-6-({[2-(trifluoromethyl)phenyl]carbonyl}amino)-1H-benzimidazole-4-carboxylic acid (153 mg) in DMF (5 mL), were added HBTU (178 mg) and triethylamine (65 μL). To the mixture was added 3-chloro-2-methylaniline (56 μL) under stirring at room temperature, and the mixture was stirred overnight. The reaction mixture was poured into saturated aqueous sodium bicarbonate, and extracted with ethyl acetate. The ethyl acetate layer was washed sequentially with water and brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified on silica gel column chromatography to obtain N-(3-chloro-2-methylphenyl)-2-(methoxymethyl)-6-({[2-(trifluoromethyl)phenyl]carbonyl}amino)-1H-benzimidazole-4-carboxamide (165 mg) as colorless powder.

Workup

  1. stirringthe mixture was stirred overnight
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed sequentially with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified on silica gel column chromatography

Sources & evidence

ORD record
ord-b3467955550c47bf8d25d926ba6d05cd
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09216968B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes