Diisopropylethylamine → tert-butyl 3-[({[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino)carbonyl)amino]-1-pyrrolidinecarboxylate

HRID 1247822Notes

Reaction equation

HRID 1247822 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.[NH2:37][CH:38]1[CH2:42][CH2:41][N:40]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:39]1.C(N(C(C)C)C(C)C)C>C(Cl)Cl>[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]([NH:37][CH:38]2[CH2:42][CH2:41][N:40]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:39]2)=[O:29])[CH:4]=[N:3]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27563701-Boc-3-aminopyrrolidineHCID 21904567Phenyl [1-methyl-5-(tritylamino)pyrazol-4-yl]carbamate

Product 1

HCID 21904584tert-butyl 3-[({[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino)carbonyl)amino]-1-pyrrolidinecarboxylateYield 60.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of phenyl [1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]carbamate (711 mg) and tert-butyl 3-amino-1-pyrrolidinecarboxylate (372 mg) in methylenechloride (15 ml) was added N-ethyldiisopropylamine (0.51 ml), and the mixture was stirred under reflux for 17 hours. The reaction mixture was washed successively with 10% aqueous citric acid solution, brine and saturated aqueous sodium hydrogen carbonate solution. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with 10% methanol/methylenechloride to give tert-butyl 3-[({[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}carbonyl)amino]-1-pyrrolidinecarboxylate (511 mg) as a solid.

Workup

  1. temperatureunder reflux for 17 hours
  2. washThe reaction mixture was washed successively with 10% aqueous citric acid solution, brine and saturated aqueous sodium hydrogen carbonate solution
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel eluting with 10% methanol/methylenechloride

Sources & evidence

ORD record
ord-44b48c00dfb94c01a5ea46f11dcda237
Source dataset
uspto-grants-2006_10
Patent number
US07129232B2

Reaction notes

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