N-[4-(benzyloxy)phenyl]pyridine-2-carboxamide → 1H-Pyrazole-3-carboxamide, 5-methyl-N-[4-(phenylmethoxy)phenyl]-

HRID 1474510Notes

Reaction equation

HRID 1474510 reaction equation
Cl.C(OC1C=CC(N)=CC=1)C1C=CC=CC=1.[CH3:17][C:18]1[CH:19]=[CH:20][N:21](C(O)=O)[N:22]=1.[CH2:26]([O:33][C:34]1[CH:39]=[CH:38][C:37]([NH:40][C:41](C2C=CC=CN=2)=[O:42])=[CH:36][CH:35]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[CH2:26]([O:33][C:34]1[CH:39]=[CH:38][C:37]([NH:40][C:41]([C:20]2[CH:19]=[C:18]([CH3:17])[NH:22][N:21]=2)=[O:42])=[CH:36][CH:35]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

4

Reactant 3

HCID 2425421N-[4-(benzyloxy)phenyl]pyridine-2-carboxamideHCID 27238314-Benzyloxyaniline hydrochlorideHCID 220502645-Methylpyrazole-2-carboxylic acid

Product 1

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

Procedure

This compound was prepared from 4-benzyloxyaniline hydrochloride (4.0 g, 17.0 mmol) and 5-methylpyrazole-2-carboxylic acid (2.25 g, 17.8 mmol), using the same method used to prepare pyridine-2-carboxylic acid (4-benzyloxyphenyl)amide, to give the product as a solid. The product was used without further purification in the subsequent reaction. MS m/z 308 (MH+). 1H NMR(CDCl3+MeOD-d4) δ 2.34 (s, 3H), 5.06 (s, 2H), 6.62 (s, 1H), 6.96 (d, 2H), 7.31 (m, 7H) and 7.58 (d, 1H).

Sources & evidence

ORD record
ord-a6a3643a547544fc9a998119eb982c46
Source dataset
uspto-grants-2015_04
Patent number
US09018241B2

Reaction notes

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