2-Chloro-N-pyrimidin-5-yl-acetamide → (R)-3-(1-Phenyl-cycloheptanecarbonyloxy)-1-(pyrimidin-5-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane chloride

HRID 2192383

Reaction equation

HRID 2192383 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.[Cl:25][CH2:26][C:27]([NH:29][C:30]1[CH:31]=[N:32][CH:33]=[N:34][CH:35]=1)=[O:28]>C(#N)C>[Cl-: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][C:27](=[O:28])[NH:29][C:30]5[CH:31]=[N:32][CH:33]=[N:34][CH:35]=5)([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 202081392-Chloro-N-pyrimidin-5-yl-acetamideHCID 591796191-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester

Product 1

HCID 86655300(R)-3-(1-Phenyl-cycloheptanecarbonyloxy)-1-(pyrimidin-5-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane chlorideYield 86.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (Example 14e) (115 mg) in acetonitrile (2 mL) was treated with 2-chloro-N-pyrimidin-5-yl-acetamide (Example 52a) (66 mg) to give a dark brown solution that was stirred at room temperature overnight. The resulting solid was filtered off, washed with cold acetonitrile (2 mL) and pentane (3 mL) and dried under vacuum at 45° C. to give the title compound as a tan solid (151 mg).

Workup

  1. customto give a dark brown solution that
  2. filtrationThe resulting solid was filtered off
  3. washwashed with cold acetonitrile (2 mL) and pentane (3 mL)
  4. customdried under vacuum at 45° C.

Sources & evidence

ORD record
ord-76e3315c2be64725aac36c468c1f53b6
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Linked notes

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