O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → N-{2,4-Dichloro-3-[5-chloro-1-methyl-6-(3-trifluoromethyl-piperidin-1-yl)-1H-benzimidazol-2-ylamino]-benzyl}-1-trifluoromethyl-cyclobutanecarboxamide

HRID 1258681Notes

Reaction equation

HRID 1258681 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[F:23][C:24]([F:33])([F:32])[C:25]1([C:29]([OH:31])=O)[CH2:28][CH2:27][CH2:26]1.[Cl:34][C:35]1[C:42]([NH:43][C:44]2[N:48]([CH3:49])[C:47]3[CH:50]=[C:51]([N:55]4[CH2:60][CH2:59][CH2:58][CH:57]([C:61]([F:64])([F:63])[F:62])[CH2:56]4)[C:52]([Cl:54])=[CH:53][C:46]=3[N:45]=2)=[C:41]([Cl:65])[CH:40]=[CH:39][C:36]=1[CH2:37][NH2:38]>CN(C=O)C>[Cl:34][C:35]1[C:42]([NH:43][C:44]2[N:48]([CH3:49])[C:47]3[CH:50]=[C:51]([N:55]4[CH2:60][CH2:59][CH2:58][CH:57]([C:61]([F:64])([F:63])[F:62])[CH2:56]4)[C:52]([Cl:54])=[CH:53][C:46]=3[N:45]=2)=[C:41]([Cl:65])[CH:40]=[CH:39][C:36]=1[CH2:37][NH:38][C:29]([C:25]1([C:24]([F:23])([F:33])[F:32])[CH2:26][CH2:27][CH2:28]1)=[O:31]

Participants

5

Reactant 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27828381-(Trifluoromethyl)cyclobutanecarboxylic acidHCID 866743352,4-Dichloro-3-[5-chloro-1-methyl-6-(3-(trifluoromethyl)piperidin-1-yl)-1H-benzimidazol-2-ylamino]benzylamine

Product 1

HCID 88538224N-{2,4-Dichloro-3-[5-chloro-1-methyl-6-(3-trifluoromethyl-piperidin-1-yl)-1H-benzimidazol-2-ylamino]-benzyl}-1-trifluoromethyl-cyclobutanecarboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared from TBTU (35 mg, 0.11 mmol), TEA (50 μL, 0.36 mmol), 1-trifluormethyl-cyclobutanecarboxylic acid (57 mg, 0.4 mmol) and 2,4-dichloro-3-[5-chloro-1-methyl-6-(3-(trifluoromethyl)piperidin-1-yl)-1H-benzimidazol-2-ylamino]benzylamine (45.3 mg, 0.1 mmol) in DMF (3 mL) analogy to example 1 step (i).

Sources & evidence

ORD record
ord-6d323e32c57a4a44871d44b75eb86c4c
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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