Diisopropylethylamine → [2,2-Dimethyl-4-(3-methylamino-4-nitro-benzoyl)-piperazin-1-yl]-(1-phenyl-1H-[1,2,4]-triazol-3-yl)-methanone

HRID 334072Notes

Reaction equation

HRID 334072 reaction equation
FC(F)(F)C(O)=O.[CH3:8][C:9]1([CH3:28])[CH2:14][NH:13][CH2:12][CH2:11][N:10]1[C:15]([C:17]1[N:21]=[CH:20][N:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:18]=1)=[O:16].[CH3:29][NH:30][C:31]1[CH:32]=[C:33]([CH:37]=[CH:38][C:39]=1[N+:40]([O-:42])=[O:41])[C:34](O)=[O:35].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:8][C:9]1([CH3:28])[CH2:14][N:13]([C:34](=[O:35])[C:33]2[CH:37]=[CH:38][C:39]([N+:40]([O-:42])=[O:41])=[C:31]([NH:30][CH3:29])[CH:32]=2)[CH2:12][CH2:11][N:10]1[C:15]([C:17]1[N:21]=[CH:20][N:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:18]=1)=[O:16]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 221846233-(Methylamino)-4-nitrobenzoic acidHCID 86688259(2,2-dimethyl-piperazin-1-yl)-(1-phenyl-1-H-[1,2,4]triazol-3-yl)-methanone trifluoroacetate

Product 1

HCID 86688294[2,2-Dimethyl-4-(3-methylamino-4-nitro-benzoyl)-piperazin-1-yl]-(1-phenyl-1H-[1,2,4]-triazol-3-yl)-methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 399 mg (1.00 mmol) (2,2-dimethyl-piperazin-1-yl)-(1-phenyl-1-H-[1,2,4]triazol-3-yl)-methanone trifluoroacetate, 196 mg (1.00 mmol) 3-methylamino-4-nitro-benzoic acid, 353 mg (1.10 mmol) TBTU and 600 μL (3.50 mmol) DIPEA in 1.00 mL DMF was stirred at RT for 1 h. The reaction mixture was poured into ice water. The precipitate was filtered off, washed with water and dried.

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-f786e7b19b824260832496b5d328a140
Source dataset
uspto-grants-2014_11
Patent number
US08883789B2

Reaction notes

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