2-bromo-N-(isoxazol-3-yl)acetamide → HCID 44472504, compound

HRID 2192327Notes

Reaction equation

HRID 2192327 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:35]=[CH:34][O: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:35]=[CH:34][O: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 133629192-bromo-N-(isoxazol-3-yl)acetamideHCID 58348365HCID 58348365, compound

Product 1

HCID 44472504HCID 44472504, compoundYield 60.2%

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) (50 mg) and 2-bromo-N-isoxazol-3-yl-acetamide (Example 13a) (30 mg) were dissolved in acetonitrile (4 mL) and stirred overnight. The solution was diluted with diethyl ether (12 mL) and stirred overnight. The resulting crystals were filtered off, washed with ether (3×10 mL) and dried to afford the titled compound as a solid (48 mg).

Workup

  1. stirringstirred overnight
  2. filtrationThe resulting crystals were filtered off
  3. washwashed with ether (3×10 mL)
  4. customdried

Sources & evidence

ORD record
ord-c830be3f8aca441a93f8d762f6fb9ba6
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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