1,4-Dimethyl-1H-pyrazol-5-amine → HCID 9945354, compound

HRID 2270129Notes

Reaction equation

HRID 2270129 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:15]([OH:17])=O)=[C:7]2[C:11]=1[O:10][C:9]([CH2:12][O:13][CH3:14])=[CH:8]2.[CH3:18][N:19]1[C:23]([NH2:24])=[C:22]([CH3:25])[CH:21]=[N:20]1>>[CH3:18][N:19]1[C:23]([NH:24][C:15]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[C:11]3[O:10][C:9]([CH2:12][O:13][CH3:14])=[CH:8][C:7]=23)=[O:17])=[C:22]([CH3:25])[CH:21]=[N:20]1

Participants

3

Reactant 2

HCID 128479481,4-Dimethyl-1H-pyrazol-5-amineHCID 18423641HCID 18423641, compound

Product 1

HCID 9945354HCID 9945354, compoundYield 28%

Procedure

Starting from 7-methoxy-2-methoxymethylbenzofuran-4-carboxylic acid (0.1 g) and 2,4-dimethyl-2-H-pyrazol-3-ylamine (56 mg). Purification by column chromatography on silica eluting with 20% heptane in ethyl acetate and gradient preparative HPLC on a Phenomenex LUNA(2)™ C18 column eluting with 0.05% trifluoroacetic acid in 20%-65% acetonitrile in water gave the title compound as a pale yellow solid (39 mg).

Workup

  1. customPurification by column chromatography on silica eluting with 20% heptane in ethyl acetate and gradient preparative HPLC on a Phenomenex LUNA(2)™ C18 column
  2. washeluting with 0.05% trifluoroacetic acid in 20%-65% acetonitrile in water

Sources & evidence

ORD record
ord-4d2ff33aadc9493d93f5ca7678e25175
Source dataset
uspto-grants-2001_12
Patent number
US06331556B2

Reaction notes

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