Benzoic Acid → N-[4-Methyl-3-(2-pyridin-3-yl-6-(trifluoromethyl)pyrimidin-4-ylamino)-phenyl]benzamide

HRID 2084182Notes

Reaction equation

HRID 2084182 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:26])=[C:7]([CH:25]=1)[NH:8][C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[N:12]=[C:11]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[N:10]=1.[C:27](O)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[CH3:26][C:6]1[CH:5]=[CH:4][C:3]([NH:2][C:27](=[O:34])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:25][C:7]=1[NH:8][C:9]1[CH:14]=[C:13]([C:15]([F:17])([F:18])[F:16])[N:12]=[C:11]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[N:10]=1

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22732477HCID 22732477, compound

Product 1

HCID 10114731N-[4-Methyl-3-(2-pyridin-3-yl-6-(trifluoromethyl)pyrimidin-4-ylamino)-phenyl]benzamideYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(5-amino-2-methylanilino)-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidine hydrochloride (25 mg, 0.067 mmol), benzoic acid (10 mg, 0.080 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (15.4 mg, 0.080 mmol) in dichloromethane (5 ml) was stirred at room temperature for 24 h. The mixture was rotary evaporated to dryness and the residue was purified by column chromatography to give a white solid (14 mg, 47%). 1H NMR (CDCl3): 9.66 (s, 1H), 8.75-8.71 (m, 1H), 8.67 (bs, 1H), 8.40 (s, 1H), 8.08 (dd, J=1.2, 8.4 Hz, 1H), 7.93 (d, J=1.8 Hz, 1H), 7.90-7.86 (m, 2H), 7.81 (s, 1H), 7.55-7.38 (m, 4H), 7.25 (d, J=8.4 Hz, 1H), 6.71 (s, 1H), 2.23 (s, 3H).

Workup

  1. customThe mixture was rotary evaporated to dryness
  2. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-cd67e9d8b8dc4079a07979f7405039aa
Source dataset
uspto-grants-2004_04
Patent number
US06716851B2

Reaction notes

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