3-Hydroxypiperidine → 2-[2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-(3-hydroxypiperidin-1-yl)-benzoylamino]-N-(5-chloropyridin-2-yl)-benzamide

HRID 644177

Reaction equation

HRID 644177 reaction equation
F[C:2]1[CH:26]=[CH:25][C:5]([C:6]([NH:8][C:9]2[CH:24]=[CH:23][CH:22]=[CH:21][C:10]=2[C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][N:15]=2)=[O:12])=[O:7])=[C:4]([O:27][CH:28]2[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]2)[CH:3]=1.[OH:41][CH:42]1[CH2:47][CH2:46][CH2:45][NH:44][CH2:43]1>>[C:37]([O:36][C:34]([N:31]1[CH2:30][CH2:29][CH:28]([O:27][C:4]2[CH:3]=[C:2]([N:44]3[CH2:45][CH2:46][CH2:47][CH:42]([OH:41])[CH2:43]3)[CH:26]=[CH:25][C:5]=2[C:6]([NH:8][C:9]2[CH:24]=[CH:23][CH:22]=[CH:21][C:10]=2[C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][N:15]=2)=[O:12])=[O:7])[CH2:33][CH2:32]1)=[O:35])([CH3:40])([CH3:39])[CH3:38]

Participants

3

Reactant 2

HCID 232933-HydroxypiperidineHCID 685302072-[4-Fluoro-2-(1-tert-butoxycarbonylpiperidin-4-yloxy)benzoylamino]-N-(5-chloropyridin-2-yl)benzamide

Product 1

HCID 685325502-[2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-(3-hydroxypiperidin-1-yl)-benzoylamino]-N-(5-chloropyridin-2-yl)-benzamideYield 34%

Procedure

Using methods substantially equivalent to those described in Example 4-F, except that the reaction was quenched with water and the resulting precipitate was collected, 2-[2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-(3-hydroxypiperidin-1-yl)-benzoylamino]-N-(5-chloropyridin-2-yl)-benzamide (166 mg, 0.26 mmol, 34%) was prepared from 2-[4-fluoro-2-(1-tert-butoxycarbonylpiperidin-4-yloxy)benzoylamino]-N-(5-chloropyridin-2-yl)benzamide and 3-hydroxypiperidine.

Workup

  1. customwas quenched with water
  2. customthe resulting precipitate was collected

Sources & evidence

ORD record
ord-e68b6706cfe54f6283b7af0227cb4111
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Linked notes

Loading…