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

HRID 1828735Notes

Reaction equation

HRID 1828735 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-amino-4-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), 7.55-7.65 (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-19d2fa2b7e05454f8a30b72257474f73
Source dataset
uspto-grants-2006_06
Patent number
US07060700B2

Reaction notes

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