N-(3-amino-4-methylphenyl)-2-morpholinopyridine-4-carboxamide → N-{3-[3-(1-tert-butoxycarbonylpyrrolidin-3-yloxy)benzamido]-4-methylphenyl}-2-morpholinopyridine-4-carboxamide

HRID 1281725Notes

Reaction equation

HRID 1281725 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=2)[C:17]([OH:19])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:23][C:24]1[CH:25]=[C:26]([NH:31][C:32]([C:34]2[CH:39]=[CH:38][N:37]=[C:36]([N:40]3[CH2:45][CH2:44][O:43][CH2:42][CH2:41]3)[CH:35]=2)=[O:33])[CH:27]=[CH:28][C:29]=1[CH3:30]>>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=2)[C:17]([NH:23][C:24]2[CH:25]=[C:26]([NH:31][C:32]([C:34]3[CH:39]=[CH:38][N:37]=[C:36]([N:40]4[CH2:41][CH2:42][O:43][CH2:44][CH2:45]4)[CH:35]=3)=[O:33])[CH:27]=[CH:28][C:29]=2[CH3:30])=[O:19])[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 17904941N-(3-amino-4-methylphenyl)-2-morpholinopyridine-4-carboxamideHCID 222911363-{[1-(tert-Butoxycarbonyl)pyrrolidin-3-yl]oxy}benzoic acid

Product 1

HCID 18422094N-{3-[3-(1-tert-butoxycarbonylpyrrolidin-3-yloxy)benzamido]-4-methylphenyl}-2-morpholinopyridine-4-carboxamide

Procedure

Using an analogous procedure to that described in the first paragraph of Example 26, 3-(1-tert-butoxycarbonylpyrrolidin-3-yloxy)benzoic acid was reacted with N-(3-amino4-methylphenyl)-2-morpholinopyridine4-carboxamide to give N-{3-[3-(1-tert-butoxycarbonylpyrrolidin-3-yloxy)benzamido]-4-methylphenyl}-2-morpholinopyridine-4-carboxamide; NMR Spectrum: (DMSOd6) 1.42 (s, 9H), 2.15 (s, 2H), 2.22 (s, 3H), 3.44 (m, 3H), 3.55 (t, 4H), 3.6 (m, 1H), 3.77 (t, 4H), 5.18 (m, 1H), 7.13 (d, 1H), 7.21 (m, 1H), 7.37 (m, 2H), 7.5 (t, 1H), 7.56 (s, 1H), 7.61 (d, 2H), 7.81 (d, 1H), 8.3 (d, 1H), 9.9 (s, 1H), 10.31 (s, 1H); Mass Spectrum: M+H+ 602.

Sources & evidence

ORD record
ord-de700c03cc0046c3bfad9327945be474
Source dataset
uspto-grants-2002_09
Patent number
US06455520B1

Reaction notes

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