2-Bromo-N-(3,5-difluorophenyl)acetamide → HCID 53311178, compound

HRID 2192360Notes

Reaction equation

HRID 2192360 reaction equation
[Br:1][CH2:2][C:3]([NH:5][C:6]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]([F:13])[CH:7]=1)=[O:4].[N:14]12[CH2:21][CH2:20][CH:17]([CH2:18][CH2:19]1)[C@@H:16]([O:22][C:23]([C:25]1([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)=[O:24])[CH2:15]2>CC#N>[Br-:1].[F:13][C:8]1[CH:7]=[C:6]([NH:5][C:3]([CH2:2][N+:14]23[CH2:21][CH2:20][CH:17]([CH2:18][CH2:19]2)[C@@H:16]([O:22][C:23]([C:25]2([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[O:24])[CH2:15]3)=[O:4])[CH:11]=[C:10]([F:12])[CH:9]=1

Participants

4

Reactant 2

HCID 231521612-Bromo-N-(3,5-difluorophenyl)acetamideHCID 591796191-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester

Product 1

HCID 53311178HCID 53311178, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-bromo-N-(3,5-difluoro-phenyl)-acetamide (42 mg) (Example 35a) and 1-phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (Example 14e) (50 mg) in MeCN (1 mL) was stirred at room temperature for 72 h. The solid precipitate was filtered off, washed with ether and dried at 50° C. under vacuum overnight. The mother liquors were evaporated, treated with ether and the resulting solid was filtered off. The solids were combined and crystallised from hot isopropyl alcohol to give the title compound (15 mg) as a colourless solid.

Workup

  1. filtrationThe solid precipitate was filtered off
  2. washwashed with ether
  3. customdried at 50° C. under vacuum overnight
  4. customThe mother liquors were evaporated
  5. additiontreated with ether
  6. filtrationthe resulting solid was filtered off
  7. customcrystallised from hot isopropyl alcohol

Sources & evidence

ORD record
ord-40cec1d02a0d40d8958b2d3d407ec4cd
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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