Water → tert-butyl 4-({[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino)carbonyl)-1-piperazinecarboxylate

HRID 1247848Notes

Reaction equation

HRID 1247848 reaction equation
[CH3:1][N:2]1[C:6]([NH:7][C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:5]([NH:27][C:28](=O)[O:29]C2C=CC=CC=2)[CH:4]=[N:3]1.C(N(CC)CC)C.[N:44]1([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]1.O>CN(C)C=O>[CH3:1][N:2]1[C:6]([NH:7][C:8]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[C:5]([NH:27][C:28]([N:47]2[CH2:48][CH2:49][N:44]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[CH2:45][CH2:46]2)=[O:29])[CH:4]=[N:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 21904567Phenyl [1-methyl-5-(tritylamino)pyrazol-4-yl]carbamate

Product 1

HCID 21904511tert-butyl 4-({[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino)carbonyl)-1-piperazinecarboxylateYield 85.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of phenyl [1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]carbamate (4.6 g) in N,N-dimethylformamide (32 ml) were added triethylamine (1.08 g) and tertbutyl 1-piperazinecarboxylate (1.99 g). The reaction mixture was stirred for 3 hours and poured into water. The mixture was extracted with ethyl acetate, and the organic layer was concentrated in vacuo. The residue was purified by column chromatography on silica gel (ethyl acetate→ethyl acetate:ethanol=20:1) to give tert-butyl 4-({[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}carbonyl)-1-piperazinecarboxylate (4.7 g)

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. concentrationthe organic layer was concentrated in vacuo
  3. customThe residue was purified by column chromatography on silica gel (ethyl acetate→ethyl acetate:ethanol=20:1)

Sources & evidence

ORD record
ord-47a6894f0d294bd9a3db2ea86671a279
Source dataset
uspto-grants-2006_10
Patent number
US07129232B2

Reaction notes

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