Trityl chloride → HCID 21904520, compound

HRID 1247832Notes

Reaction equation

HRID 1247832 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:21])[CH2:10][CH2:11][N:12]([CH3:20])[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].[C:22](Cl)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C.C(OCC)(=O)C>CN(C)C=O.CN(C)C1C=CN=CC=1>[CH3:20][N:12]([CH2:11][CH2:10][C:9]([NH:8][C:3]1[CH:4]=[N:5][N:6]([CH3:7])[C:2]=1[NH:1][C:22]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:21])[C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18]

Participants

7

Reactant 4

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 21904547HCID 21904547, compound

Product 1

HCID 21904520HCID 21904520, compoundYield 47.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl N-{3-[(5-amino-1-methyl-1H-pyrazol-4-yl)amino]-3-oxopropyl}-N-methylcarbamate (4.88 g) in N,N-dimethylformamide (50 ml) were added trityl chloride (6.86 g), triethylamine (6.86 ml) and 4-dimethylaminopyridine (80 mg) succesively. The mixture was stirred at room temperature overnight. To the resulting mixture was added ethyl acetate and washed with water (three times) and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel to give tert-butyl N-methyl-N-(3-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-3-oxopropyl)carbamate (4.20 g) as an amorphous solid.

Workup

  1. washwashed with water (three times) and brine
  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

Sources & evidence

ORD record
ord-eec169fdc79744eca20d221b2039fb49
Source dataset
uspto-grants-2006_10
Patent number
US07129232B2

Reaction notes

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