Trityl chloride → tert-butyl (3S)-3-[(([1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}carbonyl)amino]-1-pyrrolidinecarboxylate

HRID 1247828Notes

Reaction equation

HRID 1247828 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[NH:8][C:9]([NH:11][C@H:12]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13]1)=[O:10].C(N(C(C)C)C(C)C)C.[C:33](Cl)([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(Cl)(Cl)Cl>[CH3:7][N:6]1[C:2]([NH:1][C:33]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)=[C:3]([NH:8][C:9]([NH:11][C@H:12]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13]2)=[O:10])[CH:4]=[N:5]1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 81531DiisopropylethylamineHCID 86593412tert-butyl (3S)-3-({[(5-amino-1-methyl-1H-pyrazol-4-yl)amino]carbonyl}amino)-1-pyrrolidinecarboxylate

Product 1

HCID 86593411tert-butyl (3S)-3-[(([1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}carbonyl)amino]-1-pyrrolidinecarboxylateYield 54.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of tert-butyl (3S)-3-({[(5-amino-1-methyl-1H-pyrazol-4-yl)amino]carbonyl}amino)-1-pyrrolidinecarboxylate (1.8 g) and N-ethyldiisopropylamine (720 mg) in chloroform (50 ml) was added trityl chloride (1.6 g), and the mixture was stirred at room temperature for 28 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 3% methanol/chloroform to give tert-butyl (3S)-3-[({[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}carbonyl)amino]-1-pyrrolidinecarboxylate (1.7 g) as a solid.

Workup

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

Sources & evidence

ORD record
ord-9318048bd9614768bdcbf2c8e98a335e
Source dataset
uspto-grants-2006_10
Patent number
US07129232B2

Reaction notes

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