Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → N-{4-Trifluoromethyl-3-[5-chloro-1-methyl-6-(4-trifluoromethyl-piperidin-1-yl)-1H-benzimidazol-2-ylamino]-benzyl}-3,3,3-trifluoro-2-methyl-propanamide

HRID 1258729Notes

Reaction equation

HRID 1258729 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][C:4]=1[NH:11][C:12]1[N:16]([CH3:17])[C:15]2[CH:18]=[C:19]([N:23]3[CH2:28][CH2:27][CH:26]([C:29]([F:32])([F:31])[F:30])[CH2:25][CH2:24]3)[C:20]([Cl:22])=[CH:21][C:14]=2[N:13]=1.[F:35][C:36]([F:43])([F:42])[CH:37]([CH3:41])[C:38](O)=[O:39].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[F:34][C:2]([F:33])([F:1])[C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH:8][C:38](=[O:39])[CH:37]([CH3:41])[C:36]([F:43])([F:42])[F:35])=[CH:5][C:4]=1[NH:11][C:12]1[N:16]([CH3:17])[C:15]2[CH:18]=[C:19]([N:23]3[CH2:28][CH2:27][CH:26]([C:29]([F:31])([F:32])[F:30])[CH2:25][CH2:24]3)[C:20]([Cl:22])=[CH:21][C:14]=2[N:13]=1

Participants

5

Reactant 3

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 113209873,3,3-Trifluoro-2-methylpropanoic acidHCID 866743464-Trifluoromethyl-3-[5-chloro-1-methyl-6-(4-trifluoromethyl-piperidin-1-yl)-1H-benzimidazol-2-ylamino]-benzylamine

Product 1

HCID 86674347N-{4-Trifluoromethyl-3-[5-chloro-1-methyl-6-(4-trifluoromethyl-piperidin-1-yl)-1H-benzimidazol-2-ylamino]-benzyl}-3,3,3-trifluoro-2-methyl-propanamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared in analogy to the procedure in Example 94, step (c) using 4-trifluoromethyl-3-[5-chloro-1-methyl-6-(4-trifluoromethyl-piperidin-1-yl)-1H-benzimidazol-2-ylamino]-benzylamine (110 mg; 0.22 mmol), 3,3,3-trifluoro-2-methylpropanoic acid (31 mg; 0.22 mmol), HBTU (83 mg; 0.22 mmol), TEA (45 mg; 0.44 mmol), DMF (2 mL).

Sources & evidence

ORD record
ord-a1329d8161de4377aa2da2ada423285e
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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