N-1,2-Benzisoxazol-3-yl-2-chloroacetamide → HCID 86655270, compound

HRID 2192305Notes

Reaction equation

HRID 2192305 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.[O:25]1[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[C:27]([NH:34][C:35](=[O:38])[CH2:36][Cl:37])=[N:26]1>C(#N)C>[Cl-:37].[O:25]1[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[C:27]([NH:34][C:35]([CH2:36][N+:1]23[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]2)[C@@H:3]([O:9][C:10]([C:12]2([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:11])[CH2:2]3)=[O:38])=[N:26]1

Participants

4

Reactant 2

HCID 50998330N-1,2-Benzisoxazol-3-yl-2-chloroacetamideHCID 591796191-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester

Product 1

HCID 86655270HCID 86655270, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (Example 1e) (114 mg) and N-benzo[d]isoxazol-3-yl-2-chloro-acetamide (Example 4a) (89 mg) were dissolved in acetonitrile (10 mL) and left for one week. The resulting crystals were filtered off and washed with diethyl ether (3×10 mL) to afford the titled compound as a solid (120 mg).

Workup

  1. waitleft for one week
  2. filtrationThe resulting crystals were filtered off
  3. washwashed with diethyl ether (3×10 mL)

Sources & evidence

ORD record
ord-a85c81701e814154b50ebec6ebe9f2fc
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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