O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → 2-Amino-N-{4-chloro-3-[5-chloro-1-methyl-6-(3-(trifluoromethyl)piperidin-1-yl)-1H-benzo[d]imidazol-2-ylamino]benzyl}-3,3,3-trifluoro-2-methylpropanamide
Reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[NH2:23][C:24]([CH3:32])([C:28]([F:31])([F:30])[F:29])[C:25](O)=[O:26].[Cl:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38][NH2:39])=[CH:36][C:35]=1[NH:42][C:43]1[N:47]([CH3:48])[C:46]2[CH:49]=[C:50]([N:54]3[CH2:59][CH2:58][CH2:57][CH:56]([C:60]([F:63])([F:62])[F:61])[CH2:55]3)[C:51]([Cl:53])=[CH:52][C:45]=2[N:44]=1>CN(C=O)C>[NH2:23][C:24]([CH3:32])([C:28]([F:31])([F:30])[F:29])[C:25]([NH:39][CH2:38][C:37]1[CH:40]=[CH:41][C:34]([Cl:33])=[C:35]([NH:42][C:43]2[N:47]([CH3:48])[C:46]3[CH:49]=[C:50]([N:54]4[CH2:59][CH2:58][CH2:57][CH:56]([C:60]([F:63])([F:62])[F:61])[CH2:55]4)[C:51]([Cl:53])=[CH:52][C:45]=3[N:44]=2)[CH:36]=1)=[O:26]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
TBTU (106 mg, 0.3 mmol) followed by TEA (126 μL, 0.9 mmol) were added to 2-amino-3,3,3-trifluoro-2-methylpropanoic acid (57 mg, 0.4 mmol) in DMF (2 mL). After 5 min at rt a mixture of 4-chloro-3-[5-chloro-1-methyl-6-(3-(trifluoromethyl)piperidin-1-yl)-1H-benzo[d]imidazol-2-ylamino]benzylamine (142 mg, 0.3 mmol) and DMF (2 mL) was added to the reaction mixture and stirred at rt overnight. The reaction mixture was purified by chromatography to give the title compound.
Workup
- additionwas added to the reaction mixture
- customThe reaction mixture was purified by chromatography
Sources & evidence
- ORD record
- ord-2a80c969827341c58785b4583513558d
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08466186B2
Reaction notes
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