6-Chloronicotinoyl Chloride → 3-(6-chloropyrid-3-ylcarbonylamino)-4-methyl-N-(3-morpholinophenyl)benzamide

HRID 2415724Notes

Reaction equation

HRID 2415724 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]([CH:30]=[CH:31][C:32]=1[CH3:33])[C:15]([NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[CH:19]=1)=[O:16]>>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([NH:11][C:12]2[CH:13]=[C:14]([CH:30]=[CH:31][C:32]=2[CH3:33])[C:15]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[CH:19]=2)=[O:16])=[O:9])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 27821656-Chloronicotinoyl ChlorideHCID 226361453-amino-4-methyl-N-(3-morpholinophenyl)benzamide

Product 1

HCID 226361613-(6-chloropyrid-3-ylcarbonylamino)-4-methyl-N-(3-morpholinophenyl)benzamide

Procedure

Using an analogous procedure to that described in Example 33, 6-chloropyrid-3-ylcarbonyl chloride was reacted with 3-amino-4-methyl-N-(3-morpholinophenyl)benzamide to give the title compound; NMR Spectrum: (DMSOd6) 2.3 (s, 3H), 3.05 (t, 4H), 3.75 (t, 4H), 6.65-6.75 (m, 1H), 7.18 (t, 1H), 7.25-7.3 (m, 1H), 7.3-7.5 (m, 2H), 7.7 (d, 1H), 7.75-7.85 (m, 1H), 7.97 (s, 1H), 8.35-8.45 (m, 1H), 9.0 (d, 1H), 10.0-10.04 (s, 1H), 10.26-10.29 (s, 1H); Mass Spectrum: M+H+ 451.

Sources & evidence

ORD record
ord-13285283e3ee46d5b95e2a2e0a957cbc
Source dataset
uspto-grants-2004_11
Patent number
US06821965B1

Reaction notes

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