6-Chloronicotinoyl Chloride → 6-chloro-N-[5-(3-fluoro-5-morpholinobenzamido)-2-methylphenyl]pyridine-3-carboxamide

HRID 2302260Notes

Reaction equation

HRID 2302260 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:34])[C:21]2[CH:26]=[C:25]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[CH:24]=[C:23]([F:33])[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:34])[C:21]3[CH:26]=[C:25]([N:27]4[CH2:28][CH2:29][O:30][CH2:31][CH2:32]4)[CH:24]=[C:23]([F:33])[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 11450304N-(3-amino-4-methylphenyl)-3-fluoro-5-morpholinobenzamide

Product 1

HCID 220579406-chloro-N-[5-(3-fluoro-5-morpholinobenzamido)-2-methylphenyl]pyridine-3-carboxamideYield 74%

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 4 hours, 6-chloropyridine-3-carbonyl chloride was reacted with N-(3-amino-4-methylphenyl)-3-fluoro-5-morpholinobenzamide to give the title compound in 74% yield; NMR Spectrum: (DMSOd6): 2.2 (s, 3H), 3.18-3.22 (t, 4H), 3.75-3.85 (t, 4H), 6.9-7.0 (m, 1H), 7.1-7.15 (d, 1H), 7.2-7.3 (m, 2H), 7.55-7.6 (m, 1H) 7.65-7.7 (d, 1H), 7.8 (s, 1H), 8.3-8.4 (m, 1H), 8.95 (d, 1H), 10.15 (s, 1H), 10.17 (s, 1H); Mass Spectrum M+H+ 469 and 471.

Sources & evidence

ORD record
ord-c28b1c8183bf45008cb9a3449b5d9f85
Source dataset
uspto-grants-2002_08
Patent number
US06432949B1

Reaction notes

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