Dimethylformamide → 3-[5-amino-4-(3-iodo-benzoyl)-pyrazol-1-yl]-N-methoxy-4-methyl-benzamide

HRID 1959496Notes

Reaction equation

COC([O:7][CH3:8])N(C)C.[NH2:9][C:10]1[N:14]([C:15]2[CH:16]=[C:17]([CH:21]=[CH:22][C:23]=2[CH3:24])[C:18]([OH:20])=O)[N:13]=[CH:12][C:11]=1[C:25](=[O:33])[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([I:32])[CH:27]=1.C[N:35](C=O)C>>[NH2:9][C:10]1[N:14]([C:15]2[CH:16]=[C:17]([CH:21]=[CH:22][C:23]=2[CH3:24])[C:18]([NH:35][O:7][CH3:8])=[O:20])[N:13]=[CH:12][C:11]=1[C:25](=[O:33])[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([I:32])[CH:27]=1

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 78373Dimethylformamide dimethyl acetal

HCID 111550723-[5-Amino-4-(3-iodobenzoyl)-pyrazol-1-yl]-4-methylbenzoic acid

Product 1

HCID 117848203-[5-amino-4-(3-iodo-benzoyl)-pyrazol-1-yl]-N-methoxy-4-methyl-benzamide

Conditions

Temperature: 100 °C

Procedure

N,N-Dimethylformamide dimethyl acetal (10 mL) was added to the solution of 3-(3-benzyloxy-phenyl)-3-oxo-propionitrile 3 (2.5 g, 10 mmoL) in DMF (20 mL, dry) and the mixture was stirred at 100° C. for 3 hr. Solvent was removed and the residue was purified by silica gel column chromatography (EtOAc as eluent). Product 2-(3-benzyloxy-benzoyl)-3-dimethylamino-acrylonitrile 4 was obtained as a light yellow solid (2.6 g, 90%).

Workup

customSolvent was removed
customthe residue was purified by silica gel column chromatography (EtOAc as eluent)

Sources & evidence

ORD record: ord-9eed74eee8c048aebdb6effafd90cf2d
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410160B2

Reaction notes

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