HCID 11356337, compound → N-(4-hydroxyphenyl)-5-methyl-1H-pyrazole-3-carboxamide

HRID 1474511Notes

Reaction equation

HRID 1474511 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]2[CH:22]=[C:21]([CH3:23])[NH:20][N:19]=2)=[O:17])=[CH:11][CH:10]=1)C1C=CC=CC=1.OC1C=CC(NC(C2C=CC=CN=2)=O)=CC=1>>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]2[CH:22]=[C:21]([CH3:23])[NH:20][N:19]=2)=[O:17])=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 11356337HCID 11356337, compoundHCID 844789441H-Pyrazole-3-carboxamide, 5-methyl-N-[4-(phenylmethoxy)phenyl]-

Product 1

HCID 11435898N-(4-hydroxyphenyl)-5-methyl-1H-pyrazole-3-carboxamide

Procedure

This compound was prepared from 5-methyl-1H-pyrazole-3-carboxylic acid (4-benzyloxy-phenyl)-amide, using the same method used to prepare pyridine-2-carboxylic acid (4-hydroxyphenyl)amide. The product was purified by flash chromatography, on silica gel, eluted with 5 to 10% methanol in DCM as the eluant, to give the product as an off white solid, 2.75 g (68%). MS m/z 218 (MH+). 1H NMR(DMSO-d6) δ 2.28 (s, 3H), 6.47 (s, 1H), 6.71 (d, 2H), 7.55 (d, 2H), 9.19 (s, 1H), 9.67 (s, 1H) and 13.00 (s, 1H). Anal. calcd for C11H11N3O2: C, 60.08; H, 5.17; N, 19.10. Found: C, 60.00; H, 4.99; N, 19.25.

Workup

  1. customThe product was purified by flash chromatography, on silica gel
  2. washeluted with 5 to 10% methanol in DCM as the eluant
  3. customto give the product as an off white solid, 2.75 g (68%)

Sources & evidence

ORD record
ord-2bbd512c5cdf4d5cb9784ae2ca5bd338
Source dataset
uspto-grants-2015_04
Patent number
US09018241B2

Reaction notes

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