Potassium Carbonate → HCID 66761740, compound

HRID 876334Notes

Reaction equation

HRID 876334 reaction equation
[C:1]1([C:7]([NH:9][CH:10]2[CH2:15][CH:14]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)[CH2:13][N:12]([C:26]([O:28]C3C=CC([N+]([O-])=O)=CC=3)=O)[CH2:11]2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:38][C@H:39]1[O:44][C@@H:43]([CH3:45])[CH2:42][NH:41][CH2:40]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:45][CH:43]1[O:44][CH:39]([CH3:38])[CH2:40][N:41]([C:26]([N:12]2[CH2:13][CH:14]([C:16]3[CH:17]=[CH:18][C:19]([C:22]([F:25])([F:23])[F:24])=[CH:20][CH:21]=3)[CH2:15][CH:10]([NH:9][C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[O:8])[CH2:11]2)=[O:28])[CH2:42]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 6415002,6-Dimethylmorpholine, cis-HCID 667014674-Nitrophenyl 3-[(phenylcarbonyl)amino]-5-[4-(trifluoromethyl)phenyl]piperidine-1-carboxylate

Product 1

HCID 66761740HCID 66761740, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

80 mg (0.16 mmol) of 4-nitrophenyl 3-[(phenylcarbonyl)amino]-5-[4-(trifluoromethyl)phenyl]piperidine-1-carboxylate were initially charged in 1.7 ml of DMF, and 53 mg (0.47 mmol) of (2R,6S)-2,6-dimethylmorpholine and 22 mg (0.16 mmol) of potassium carbonate were added. The mixture was reacted in a microwave (Emrys Optimizer) at 150° C. for 15 min. The crude product was then purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient). Yield: 49 mg (64% of theory)

Workup

  1. customThe mixture was reacted in a microwave (Emrys Optimizer) at 150° C. for 15 min
  2. customThe crude product was then purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient)

Sources & evidence

ORD record
ord-525c9374e7f347b6848279e711fcd85c
Source dataset
uspto-grants-2015_03
Patent number
US08987248B2

Reaction notes

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