Trimethylsilyldiazomethane → HCID 59278327, compound

HRID 1698149Notes

Reaction equation

HRID 1698149 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3[CH:13]=[N:14][CH:15]=[C:16]([C:17]([NH:19][C@H:20]([C:25]4[CH:30]=[CH:29][N:28]=[C:27]([S:31]([CH3:34])(=[O:33])=[O:32])[CH:26]=4)[CH2:21][C:22]([OH:24])=[O:23])=[O:18])[C:11]=3[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[CH3:35][Si](C=[N+]=[N-])(C)C>CO.C1C=CC=CC=1>[CH3:35][O:23][C:22](=[O:24])[CH2:21][C@H:20]([NH:19][C:17]([C:16]1[C:11]2[CH:10]=[N:9][N:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[C:12]=2[CH:13]=[N:14][CH:15]=1)=[O:18])[C:25]1[CH:30]=[CH:29][N:28]=[C:27]([S:31]([CH3:34])(=[O:33])=[O:32])[CH:26]=1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 66727356HCID 66727356, compound

Product 1

HCID 59278327HCID 59278327, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

To a slurry of (S)-3-{[1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carbonyl]-amino}-3-(2-methanesulfonyl-pyridin-4-yl)-propionic acid in methanol (1 mL) and benzene (4 mL) was added a 2 M solution of (trimethylsilyl)diazomethane in hexanes (126 μL, 0.252 mmol). After 10 minutes, the mixture became homogeneous and the resulting reaction mixture was stirred at room temperature for 30 minutes. The reaction was concentrated in vacuo and the residue was purified by silica gel chromatography using a gradient of 0-8% methanol in dichloromethane to afford the title compound as a white solid.

Workup

  1. customthe resulting reaction mixture
  2. concentrationThe reaction was concentrated in vacuo
  3. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-4ba3ceef0eb84d62aab9a4d932292605
Source dataset
uspto-grants-2012_04
Patent number
US08163918B2

Reaction notes

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