5-Amino-1-methyl-1H-pyrazole-4-carbonitrile → HCID 10294503, compound

HRID 2270122Notes

Reaction equation

HRID 2270122 reaction equation
[N+](C1C=CC(O[C:11]([C:13]2[CH:14]=[CH:15][C:16]([O:27][CH:28]([F:30])[F:29])=[C:17]3[O:21][C:20]([CH:22]4[CH2:26][CH2:25][O:24][CH2:23]4)=[CH:19][C:18]=23)=[O:12])=CC=1)([O-])=O.[NH2:31][C:32]1[N:36]([CH3:37])[N:35]=[CH:34][C:33]=1[C:38]#[N:39]>O>[C:38]([C:33]1[CH:34]=[N:35][N:36]([CH3:37])[C:32]=1[NH:31][C:11]([C:13]1[CH:14]=[CH:15][C:16]([O:27][CH:28]([F:30])[F:29])=[C:17]2[O:21][C:20]([CH:22]3[CH2:26][CH2:25][O:24][CH2:23]3)=[CH:19][C:18]=12)=[O:12])#[N:39]

Participants

4

Reactant 2

HCID 2197405-Amino-1-methyl-1H-pyrazole-4-carbonitrileHCID 69836005HCID 69836005, compound

Product 1

HCID 10294503HCID 10294503, compoundYield 46.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Prepared from 7-difluoromethoxy-2-(tetrahydrofuran-3-yl)-benzofuran-4-carboxylic acid 4-nitrophenyl ester (380 mg) and 5-amino-1-methyl-1-H-pyrazole-4-carbonitrile (220 mg). The reaction was stirred for 2 hours at room temperature. Water (1 ml) was added and the solvent removed in vacuo. The residue was dissolved in ethyl acetate (50 ml) and washed with water (2×40 ml), followed by 1N hydrochloric acid (40 ml). The organic extract was dried over magnesium sulphate, filtered and preadsorbed onto silica. Purification by column chromatography on silica eluting with 70% ethyl acetate in heptane, followed by trituration with diethyl ether afforded the title compound as a white solid (170 mg).

Workup

  1. customthe solvent removed in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate (50 ml)
  3. washwashed with water (2×40 ml)
  4. extractionThe organic extract
  5. dry with materialwas dried over magnesium sulphate
  6. filtrationfiltered
  7. customPurification by column chromatography on silica eluting with 70% ethyl acetate in heptane

Sources & evidence

ORD record
ord-067200c2db264015a01bb66a057a7184
Source dataset
uspto-grants-2001_12
Patent number
US06331556B2

Reaction notes

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