Diethyl Ether → HCID 86655279, compound

HRID 2192340Notes

Reaction equation

HRID 2192340 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][N:7]=1)=[O:4].[N:13]12[CH2:20][CH2:19][CH:16]([CH2:17][CH2:18]1)[C@@H:15]([O:21][C:22]([C:24]1([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)=[O:23])[CH2:14]2.C(OCC)C>C(#N)C>[Cl-:1].[F:12][C:9]1[CH:10]=[CH:11][C:6]([NH:5][C:3]([CH2:2][N+:13]23[CH2:20][CH2:19][CH:16]([CH2:17][CH2:18]2)[C@@H:15]([O:21][C:22]([C:24]2([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)=[O:23])[CH2:14]3)=[O:4])=[N:7][CH:8]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 229347512-Chloro-N-(5-fluoro-2-pyridinyl)acetamideHCID 591796191-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester

Product 1

HCID 86655279HCID 86655279, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Chloro-N-(5-fluoro-pyridin-2-yl)-acetamide (Example 17a) (31 mg) was added to a solution of 1-phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (Example 14e) (49 mg) in acetonitrile (1 mL). The reaction mixture was stirred at room temperature overnight. Diethyl ether (2 mL) was added to the reaction mixture and the white solid was filtered off, washed several times with diethyl ether and dried under vacuum at 40° C. to give the title compound (49 mg).

Workup

  1. filtrationthe white solid was filtered off
  2. washwashed several times with diethyl ether
  3. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-801a3f4be019424b827905f4d72f6fe3
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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