N-(3-amino-4-methylphenyl)-3-fluoro-5-piperidinobenzamide → N-[5-(3-fluoro-5-piperidinobenzamido)-2-methylphenyl]-3-(1-tert-butoxycarbonylpiperidin-4-yloxy)benzamide

HRID 967898Notes

Reaction equation

HRID 967898 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=2)[C:18](O)=[O:19])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:24][C:25]1[CH:26]=[C:27]([NH:32][C:33](=[O:47])[C:34]2[CH:39]=[C:38]([N:40]3[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]3)[CH:37]=[C:36]([F:46])[CH:35]=2)[CH:28]=[CH:29][C:30]=1[CH3:31]>>[F:46][C:36]1[CH:35]=[C:34]([CH:39]=[C:38]([N:40]2[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]2)[CH:37]=1)[C:33]([NH:32][C:27]1[CH:28]=[CH:29][C:30]([CH3:31])=[C:25]([NH:24][C:18](=[O:19])[C:17]2[CH:21]=[CH:22][CH:23]=[C:15]([O:14][CH:11]3[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:13][CH2:12]3)[CH:16]=2)[CH:26]=1)=[O:47]

Participants

3

Reactant 2

HCID 22291065N-(3-amino-4-methylphenyl)-3-fluoro-5-piperidinobenzamideHCID 222910664-(3-Carboxy-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 22291104N-[5-(3-fluoro-5-piperidinobenzamido)-2-methylphenyl]-3-(1-tert-butoxycarbonylpiperidin-4-yloxy)benzamideYield 59%

Procedure

Using an analogous procedure to that described in the first paragraph of Example 50, 3-(1-tert-butoxycarbonylpiperidin-4-yloxy)benzoic acid was reacted with N-(3-amino-4-methylphenyl)-3-fluoro-5-piperidinobenzamide to give N-[5-(3-fluoro-5-piperidinobenzamido)-2-methylphenyl]-3-(1-tert-butoxycarbonylpiperidin-4-yloxy)benzamide in 59% yield; NMR Spectrum: (DMSOd6) 1.38 (s, 9H), 1.59 (m, 8H), 1.95 (m, 1H), 2.19 (s, 3H), 3.20 (m, 6H), 3.64 (m, 2H), 4.63 (m, 1H), 6.90 (d, 1H), 7.02 (d, 1H), 7.22 (m, 3H), 7.41 (t, 1H), 7.57 (m, 3H), 7.78 (s, 1H), 9.83 (s, 1H), 10.13 (s, 1H); Mass Spectrum: M+H+ 631.

Sources & evidence

ORD record
ord-147799ca1f4141b2bf3a3301b51e62a0
Source dataset
uspto-grants-2005_10
Patent number
US06956037B2

Reaction notes

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