Succinimido 1-t-butoxycarbonylpiperidine-4-carboxylate → tert-butyl 4-({[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino)carbonyl)-1-piperidinecarboxylate

HRID 1247830Notes

Reaction equation

HRID 1247830 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]([NH2:27])[CH:4]=[N:3]1.O=C1CCC(=O)N1[O:35][C:36]([CH:38]1[CH2:43][CH2:42][N:41]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:40][CH2:39]1)=O>ClCCl>[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:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:5]([NH:27][C:36]([CH:38]2[CH2:43][CH2:42][N:41]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:40][CH2:39]2)=[O:35])[CH:4]=[N:3]1

Participants

4

Reactant 2

HCID 15578030Succinimido 1-t-butoxycarbonylpiperidine-4-carboxylateHCID 685167251-methyl-N5-trityl-1H-pyrazole-4,5-diamine

Product 1

HCID 21904535tert-butyl 4-({[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino)carbonyl)-1-piperidinecarboxylateYield 28.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-methyl-N5-trityl-1H-pyrazole-4,5-diamine (4 g) in dichloromethane (100 ml) was added tert-butyl 4-{[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl}-1-piperidinecarboxylate (4.05 g), and the mixture was refluxed for 72 hours. The reaction mixture was washed successively with water 10% aqueous citric acid solution, water and brine. The extract was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give tert-butyl 4-({[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}carbonyl)-1-piperidinecarboxylate (1.806 g).

Workup

  1. temperaturethe mixture was refluxed for 72 hours
  2. washThe reaction mixture was washed successively with water 10% aqueous citric acid solution, water and brine
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2892b00def53486d98ca78a9a28d16d6
Source dataset
uspto-grants-2006_10
Patent number
US07129232B2

Reaction notes

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