Dimethylformamide → HCID 178519259, compound

HRID 538059Notes

Reaction equation

HRID 538059 reaction equation
[NH2:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([CH:19]3[CH2:21][CH2:20]3)=[O:18])[CH2:13][CH2:12]2)=[O:10])[CH2:5][CH2:4]1.CN(C=O)C.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[C:30](F)[CH:29]=1>>[Cl:27][C:28]1[CH:29]=[CH:30][C:31]([N+:34]([O-:36])=[O:35])=[C:32]([NH:1][CH2:2][C@H:3]2[CH2:8][CH2:7][C@H:6]([C:9]([N:11]3[CH2:16][CH2:15][N:14]([C:17]([CH:19]4[CH2:20][CH2:21]4)=[O:18])[CH2:13][CH2:12]3)=[O:10])[CH2:5][CH2:4]2)[CH:33]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 696914-Chloro-2-fluoro-1-nitrobenzeneHCID 178511255HCID 178511255, compound

Product 1

HCID 178519259HCID 178519259, compoundYield 83.6%

Conditions

Temperature
90 °C

Procedure

To a solution of (trans-4-aminomethyl-cyclohexyl)-(4-cyclopropanecarbonyl-piperazin-1-yl)-methanone (600 mg, 2.1 mmol) in DMF (5 mL) K2CO3 (565 mg, 4.1 mmol) and 4-chloro-2-fluoronitrobenzene (360 mg, 2.1 mmol) were added and the mixture was heated at 90° C. for 4 hours. Then the solvent was removed under reduced pressure and the residue was washed with 7 mL of H2O and the precipitate was filtered affording 788 mg of the titled compound (78% yield).

Workup

  1. customThen the solvent was removed under reduced pressure
  2. washthe residue was washed with 7 mL of H2O
  3. filtrationthe precipitate was filtered

Sources & evidence

ORD record
ord-3f0718686c9d49349c50bc238479344b
Source dataset
uspto-grants-2014_10
Patent number
US08865704B2

Reaction notes

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