Diethyl Ether → HCID 53311172, compound

HRID 2192352Notes

Reaction equation

HRID 2192352 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][N:9]=[N:8][CH:7]=1)=[O:4].[N:12]12[CH2:19][CH2:18][CH:15]([CH2:16][CH2:17]1)[C@@H:14]([O:20][C:21]([C:23]1([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)=[O:22])[CH2:13]2.C(OCC)C>C(#N)C>[CH:21]([O-:22])=[O:20].[C:30]1([C:23]2([C:21]([O:20][C@@H:14]3[CH:15]4[CH2:18][CH2:19][N+:12]([CH2:2][C:3](=[O:4])[NH:5][C:6]5[CH:11]=[CH:10][N:9]=[N:8][CH:7]=5)([CH2:17][CH2:16]4)[CH2:13]3)=[O:22])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 591796191-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)esterHCID 67311698HCID 67311698, compound

Product 1

HCID 53311172HCID 53311172, compoundYield 24.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Chloro-N-pyridazin-4-yl-acetamide (Example 27a) (58 mg) was added to a solution of 1-phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (Example 14e) (100 mg) in acetonitrile (2 mL). The reaction mixture was allowed to stir at room temperature for 24 h. Diethyl ether (2 mL) was added to the reaction mixture and stirred for 15 minutes. The solid was filtered off, washed with diethyl ether, and dried under vacuum at 40° C. overnight. The filtrate was evaporated, combined with the solid and purified by column chromatography, eluting with 0-15% MeOH/dichloromethane. Further purification by reverse-phase prep HPLC with gradient elution from 15% MeCN/H2O containing 0.1% formic acid increasing by 1% per minute gave the title compound (19 mg) as a colourless gum.

Workup

  1. stirringstirred for 15 minutes
  2. filtrationThe solid was filtered off
  3. washwashed with diethyl ether
  4. customdried under vacuum at 40° C. overnight
  5. customThe filtrate was evaporated
  6. custompurified by column chromatography
  7. washeluting with 0-15% MeOH/dichloromethane
  8. customFurther purification by reverse-phase prep HPLC
  9. washwith gradient elution from 15% MeCN/H2O containing 0.1% formic acid increasing by 1% per minute

Sources & evidence

ORD record
ord-ea840ed68d984ef49b4e51ff02b0a984
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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