5-Amino-1-methyl-1H-pyrazole-4-carbonitrile → HCID 10112717, compound

HRID 2186465Notes

Reaction equation

HRID 2186465 reaction equation
[N+](C1C=CC([O:10][C:11]([C:13]2[C:21]3[O:20][C:19]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[N:18][C:17]=3[C:16]([O:28][CH:29]([F:31])[F:30])=[CH:15][CH:14]=2)=O)=CC=1)([O-])=O.[NH2:32][C:33]1[N:37]([CH3:38])[N:36]=[CH:35][C:34]=1[C:39]#[N:40]>>[C:39]([C:34]1[CH:35]=[N:36][N:37]([CH3:38])[C:33]=1[NH:32][C:11]([C:13]1[C:21]2[O:20][C:19]([N:22]3[CH2:23][CH2:24][O:25][CH2:26][CH2:27]3)=[N:18][C:17]=2[C:16]([O:28][CH:29]([F:31])[F:30])=[CH:15][CH:14]=1)=[O:10])#[N:40]

Participants

3

Reactant 2

HCID 2197405-Amino-1-methyl-1H-pyrazole-4-carbonitrileHCID 69839296HCID 69839296, compound

Product 1

HCID 10112717HCID 10112717, compoundYield 29.1%

Procedure

Starting from 4-difluoromethoxy-2-(morpholin-4-yl)-benzooxazole-7-carboxylic acid 4-nitrophenyl ester (100 mg) and 5-amino-1-methyl-1H-pyrazole-4-carbonitrile (56 mg). Purification by column chromatography on silica eluting with 5% methanol in dichloromethane followed by preparative thin layer chromatography eluting with 3% methanol in dichloromethane afforded the title compound as a white solid (28 mg).

Workup

  1. customPurification by column chromatography on silica eluting with 5% methanol in dichloromethane
  2. washeluting with 3% methanol in dichloromethane

Sources & evidence

ORD record
ord-87f9a1ecea3a4762b69024a9afedd186
Source dataset
uspto-grants-2002_06
Patent number
US06403791B1

Reaction notes

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