N-1,2-Benzisoxazol-3-yl-2-chloroacetamide → (R)-1-(Benzo[d]isoxazol-3-ylcarbamoylmethyl)-3-(1-thiophen-2-yl-cycloheptanecarbonyloxy)-1-azonia-bicyclo[2.2.2]octane chloride

HRID 2192318Notes

Reaction equation

HRID 2192318 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[S:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11])[CH2:2]2.[O:24]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[C:26]([NH:33][C:34](=[O:37])[CH2:35][Cl:36])=[N:25]1>C(#N)C>[Cl-:36].[O:24]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[C:26]([NH:33][C:34]([CH2:35][N+:1]23[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]2)[C@@H:3]([O:9][C:10]([C:12]2([C:19]4[S:20][CH:21]=[CH:22][CH:23]=4)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:11])[CH2:2]3)=[O:37])=[N:25]1

Participants

4

Reactant 2

HCID 50998330N-1,2-Benzisoxazol-3-yl-2-chloroacetamideHCID 58348375HCID 58348375, compound

Product 1

HCID 86655275(R)-1-(Benzo[d]isoxazol-3-ylcarbamoylmethyl)-3-(1-thiophen-2-yl-cycloheptanecarbonyloxy)-1-azonia-bicyclo[2.2.2]octane chlorideYield 70.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Thiophen-2-yl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (Example 5d) (71 mg) and N-benzo[d]isoxazol-3-yl-2-chloro-acetamide (Example 4a) (54 mg) were dissolved in acetonitrile (10 mL) and left to stand for 6 days. The resulting crystals were filtered off and washed with diethyl ether (3×10 mL) to afford the titled compound (82 mg).

Workup

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

Sources & evidence

ORD record
ord-9f29a7bcdfda453ea18e4508190b2bbd
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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