Water → HCID 86593419, compound

HRID 1247847Notes

Reaction equation

HRID 1247847 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][CH2:8][F:9])[N:5]=[CH:4][C:3]=1[NH:10][C:11](=[O:22])[CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18].C(N(CC)CC)C.[C:30](Cl)([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.O>CN(C)C=O.CN(C)C1C=CN=CC=1>[F:9][CH2:8][CH2:7][N:6]1[C:2]([NH:1][C:30]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)=[C:3]([NH:10][C:11](=[O:22])[CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:18])[CH3:20])[CH:4]=[N:5]1

Participants

7

Reactant 4

HCID 962WaterHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 86593418HCID 86593418, compound

Product 1

HCID 86593419HCID 86593419, compoundYield 49.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl (3-{[5-amino-1-(2-fluoroethyl)-1H-pyrazol-4-yl]amino}-3-oxopropyl)carbamate (2.3 g) in N,N-dimethylformamide (12 ml) were added triethylamine (1.48 g), 4-dimethylaminopyridine (35.6 mg) and trityl chloride (2.2 g) at room temperature. The reaction mixture was stirred for 2 hours, and water was added. The mixture was extracted with ethyl acetate, and the organic layer was washed with water and aqueous sodium chloride solution. The organic layer was dried over magnesium sulfate and concentrated in vacuo. Acetonitrile was added, and the precipitate was collected by filtration to give tert-butyl (3-{[1-(2-fluoroethyl)-5-(tritylamino)-1H-pyrazol-4-yl]amino}-3-oxopropyl)carbamate (2 g).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with water and aqueous sodium chloride solution
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. additionAcetonitrile was added
  6. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-9ead8a85dc9547ce8bf9d5cf91bdf0e7
Source dataset
uspto-grants-2006_10
Patent number
US07129232B2

Reaction notes

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