N-(1,3-dimethylpyrazol-4-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine → HCID 58336551, compound

HRID 1045975Notes

Reaction equation

HRID 1045975 reaction equation
[NH2:1][C:2]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:3]=1[C:4]([NH:6][O:7][CH3:8])=[O:5].[CH3:14][N:15]1[CH:19]=[C:18]([NH:20][C:21]2[CH:26]=[C:25](I)[C:24]([C:28]([F:31])([F:30])[F:29])=[CH:23][N:22]=2)[C:17]([CH3:32])=[N:16]1>>[CH3:14][N:15]1[CH:19]=[C:18]([NH:20][C:21]2[CH:26]=[C:25]([NH:1][C:2]3[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:3]=3[C:4]([NH:6][O:7][CH3:8])=[O:5])[C:24]([C:28]([F:30])([F:29])[F:31])=[CH:23][N:22]=2)[C:17]([CH3:32])=[N:16]1

Participants

3

Reactant 2

HCID 56951658N-(1,3-dimethylpyrazol-4-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amineHCID 649746092-amino-4-fluoro-N-methoxybenzamide

Product 1

HCID 58336551HCID 58336551, compoundYield 39.6%

Procedure

2-amino-4-fluoro-N-methoxybenzamide (90 mg, 0.49 mmol) and N-(1,3-dimethylpyrazol-4-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (110 mg, 0.29 mmol) were reacted according to the procedure of example 14.01. After chromatography, the solvent was evaporated to dryness, the residue triturated in tBuOMe and the resulting precipitate was collected by filtration and dried to a constant weight to afford the title compound (50 mg, 39.6%) as a white solid. NMR Spectrum: (DMSO-d6) 2.08 (s, 3H), 3.70 (s, 3H), 3.71 (s, 3H), 6.71 (bs, 1H), 6.93 (ddd, 1H), 7.36 (dd, 1H), 7.66 (dd, 1H), 7.87 (s, 1H), 8.24 (1, 1H), 8.52 (s, 1H), 9.99 (bs, 1H), 11.95 (s, 1H); Mass spectrum: MH+ 439

Workup

  1. customAfter chromatography, the solvent was evaporated to dryness
  2. customthe residue triturated in tBuOMe
  3. filtrationthe resulting precipitate was collected by filtration
  4. customdried to a constant weight

Sources & evidence

ORD record
ord-20000bd2bcb7481da1f13abc0225759c
Source dataset
uspto-grants-2013_10
Patent number
US08569298B2

Reaction notes

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