2-bromo-N-(pyrazin-2-yl)acetamide → HCID 44516992, compound

HRID 2192325Notes

Reaction equation

HRID 2192325 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]=[C:21]([F:25])[CH:20]=3)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11])[CH2:2]2.[Br:26][CH2:27][C:28]([NH:30][C:31]1[CH:36]=[N:35][CH:34]=[CH:33][N:32]=1)=[O:29]>C(#N)C.C(OCC)C>[Br-:26].[F:25][C:21]1[CH:20]=[C:19]([C:12]2([C:10]([O:9][C@@H:3]3[CH:4]4[CH2:5][CH2:6][N+:1]([CH2:27][C:28](=[O:29])[NH:30][C:31]5[CH:36]=[N:35][CH:34]=[CH:33][N:32]=5)([CH2:8][CH2:7]4)[CH2:2]3)=[O:11])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 445426692-bromo-N-(pyrazin-2-yl)acetamideHCID 58348365HCID 58348365, compound

Product 1

HCID 44516992HCID 44516992, compoundYield 62.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

1-(3-Fluoro-phenyl)-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (Example 12d) (0.100 g) was dissolved in acetonitrile (8 mL) and 2-bromo-N-pyrazin-2-yl-acetamide (Example 11a) (0.05 g) was added. The reaction mixture was stirred for 3 days diluted with diethyl ether (8 mL), stirred for a further 10 minutes, the resulting solid was filtered and washed with diethyl ether (3×8 mL) to afford a solid which was recrystallised from hot butanone (8 mL) to afford the titled compound as a solid (0.081 g).

Workup

  1. stirringstirred for a further 10 minutes
  2. filtrationthe resulting solid was filtered
  3. washwashed with diethyl ether (3×8 mL)
  4. customto afford a solid which
  5. customwas recrystallised from hot butanone (8 mL)

Sources & evidence

ORD record
ord-bc1606ecff684271b38d5cd48c3efc36
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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