N-(3-Bromopropyl)-2-pyridinecarboxamide → HCID 67311727, compound

HRID 2192393Notes

Reaction equation

HRID 2192393 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10]([C:12]1([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11])[CH2:2]2.[Br:25][CH2:26][CH2:27][CH2:28][NH:29][C:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=1)=[O:31]>CC#N>[Br-:25].[C:19]1([C:12]2([C:10]([O:9][C@@H:3]3[CH:4]4[CH2:7][CH2:8][N+:1]([CH2:26][CH2:27][CH2:28][NH:29][C:30]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=5)=[O:31])([CH2:6][CH2:5]4)[CH2:2]3)=[O:11])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 12983474N-(3-Bromopropyl)-2-pyridinecarboxamideHCID 591796191-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester

Product 1

HCID 67311727HCID 67311727, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (Example 14e) (0.31 mmol) and pyridine-2-carboxylic acid (3-bromo-propyl)-amide (Example 57b (0.31 mmol) were stirred together in anhydrous MeCN (3 mL) at room temperature for 16 days. The reaction mixture was concentrated in vacuo and the solid purified by silica gel chromatography eluting with 0-15% MeOH/dichloromethane to give the title compound (145 mg) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe solid purified by silica gel chromatography
  3. washeluting with 0-15% MeOH/dichloromethane

Sources & evidence

ORD record
ord-8ef825ce5bf842b1abd58f8579edf26c
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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