6-Chloronicotinoyl Chloride → 6-chloro-N-[2-methyl-5-(3-morpholino-5-trifluoromethylbenzamido)phenyl]pyridine-3-carboxamide

HRID 2302261Notes

Reaction equation

HRID 2302261 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8](Cl)=[O:9])=[CH:4][CH:3]=1.[NH2:11][C:12]1[CH:13]=[C:14]([NH:19][C:20](=[O:37])[C:21]2[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:23]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)[CH:22]=2)[CH:15]=[CH:16][C:17]=1[CH3:18]>>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([NH:11][C:12]2[CH:13]=[C:14]([NH:19][C:20](=[O:37])[C:21]3[CH:26]=[C:25]([C:27]([F:28])([F:29])[F:30])[CH:24]=[C:23]([N:31]4[CH2:32][CH2:33][O:34][CH2:35][CH2:36]4)[CH:22]=3)[CH:15]=[CH:16][C:17]=2[CH3:18])=[O:9])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 27821656-Chloronicotinoyl ChlorideHCID 22057990N-(3-amino4-methylphenyl)-3-morpholino-5-trifluoromethylbenzamide

Product 1

HCID 220580006-chloro-N-[2-methyl-5-(3-morpholino-5-trifluoromethylbenzamido)phenyl]pyridine-3-carboxamideYield 63%

Conditions

Temperature
100 °C

Procedure

Using an analogous procedure to that described in Example 2 except that the reaction mixture was heated to 100° C. for 2 hours, 6-chloropyridine-3-carbonyl chloride was reacted with N-(3-amino4-methylphenyl)-3-morpholino-5-trifluoromethylbenzamide. The reaction mixture was partitioned between ethyl acetate and water. The organic phase was dried over magnesium sulphate and evaporated. The residue was triturated under a mixture of isohexane and diethyl ether. There was thus obtained the title compound in 63% yield; NMR Spectrum: (DMSOd6): 2.2 (s, 3H), 3.3 (m, 4H) 3.75 (t, 4H), 7.25 (d, 1H), 7.35 (s, 1H), 755-7.65 (m, 1H), 7.65 (s, 1H), 7.7-7.75 (m, 2H), 7.8 (d, 1H), 8.35-8.4 (m, 1H), 8.95 (d, 1H), 10.15 (s, 1H), 10.33 (s, 1H); Mass Spectrum M+H+ 519 and 521.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. dry with materialThe organic phase was dried over magnesium sulphate
  3. customevaporated
  4. customThe residue was triturated under a mixture of isohexane and diethyl ether

Sources & evidence

ORD record
ord-af9715435f0c497d8a7812e37de48768
Source dataset
uspto-grants-2002_08
Patent number
US06432949B1

Reaction notes

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