O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → N-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethyl]-4-(pyrazolidin-3-on-1-yl)-3-trifluoromethyl-benzamide

HRID 1629909Notes

Reaction equation

HRID 1629909 reaction equation
[N:1]1([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][C:8]=2[C:16]([F:19])([F:18])[F:17])[CH2:5][CH2:4][C:3](=[O:6])[NH:2]1.[Cl:20][C:21]1[CH:32]=[CH:31][C:24]2[NH:25][C:26]([C@@H:28]([NH2:30])[CH3:29])=[N:27][C:23]=2[CH:22]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[Cl:20][C:21]1[CH:32]=[CH:31][C:24]2[NH:25][C:26]([C@@H:28]([NH:30][C:11](=[O:13])[C:10]3[CH:14]=[CH:15][C:7]([N:1]4[CH2:5][CH2:4][C:3](=[O:6])[NH:2]4)=[C:8]([C:16]([F:19])([F:18])[F:17])[CH:9]=3)[CH3:29])=[N:27][C:23]=2[CH:22]=1

Participants

5

Reactant 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 42034613(S)-1-(5-chloro-1H-benzimidazol-2-yl)ethylamineHCID 67048350HCID 67048350, compound

Product 1

HCID 178462091N-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethyl]-4-(pyrazolidin-3-on-1-yl)-3-trifluoromethyl-benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared analogously to Example 1f from the 4-(pyrazolidin-3-on-1-yl)-3-trifluoromethyl-benzoic acid and (1S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamine with TBTU and TEA in DMF.

Sources & evidence

ORD record
ord-23e7d375b4a4467999e5d00655fc8a93
Source dataset
uspto-grants-2014_07
Patent number
US08791103B2

Reaction notes

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