Potassium Carbonate → N-[(3RS,4SR)-4-(3,4-Dichloro-phenyl)-1-(1-ethanesulfonyl-piperidine-4-carbonyl)-pyrrolidin-3-yl]-4-methoxy-N-methyl-3-trifluoromethyl-benzamide

HRID 1951127Notes

Reaction equation

HRID 1951127 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:13][N:12]([C:14]([CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[O:15])[CH2:11][CH:10]2[N:22]([CH3:37])[C:23](=[O:36])[C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([C:32]([F:35])([F:34])[F:33])[CH:25]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(=O)([O-])[O-].[K+].[K+].[CH2:44]([S:46](Cl)(=[O:48])=[O:47])[CH3:45]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:13][N:12]([C:14]([CH:16]3[CH2:21][CH2:20][N:19]([S:46]([CH2:44][CH3:45])(=[O:48])=[O:47])[CH2:18][CH2:17]3)=[O:15])[CH2:11][CH:10]2[N:22]([CH3:37])[C:23](=[O:36])[C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([C:32]([F:33])([F:34])[F:35])[CH:25]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11667Ethanesulfonyl chlorideHCID 67025720N-[(3RS,4SR)-4-(3,4-dichloro-phenyl)-1-(piperidine-4-carbonyl)-pyrrolidin-3-yl]-4-methoxy-N-methyl-3-trifluoromethyl-benzamide

Product 1

HCID 67025950N-[(3RS,4SR)-4-(3,4-Dichloro-phenyl)-1-(1-ethanesulfonyl-piperidine-4-carbonyl)-pyrrolidin-3-yl]-4-methoxy-N-methyl-3-trifluoromethyl-benzamideYield 76%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of N-[(3RS,4SR)-4-(3,4-dichloro-phenyl)-1-(piperidine-4-carbonyl)-pyrrolidin-3-yl]-4-methoxy-N-methyl-3-trifluoromethyl-benzamide (50 mg, 0.90 mmol) in acetone (0.5 mL) was added potassium carbonate (finely milled) (19 mg, 0.13 mmol), ethanesulfonyl chloride (13 μL, 0.13 mmol) and acetone (0.5 mL). The suspension was stirred for 18 h at ambient temperature. It was diluted with ethyl acetatec (10 mL) and washed with an aqueous solution of Na2CO3 (1 M, 10 mL) and brine (10 mL). The aqueous layers were extracted with ethyl acetate (10 mL) and the combined organic layers were dried over sodium sulfate. Purification by chromatography (SiO2, heptane:ethyl acetate=30:70 to 0:100) afforded the title compound (44 mg, 76%) as an off-white foam. MS m/e: 650.2 [M]+.

Workup

  1. additionIt was diluted with ethyl acetatec (10 mL)
  2. washwashed with an aqueous solution of Na2CO3 (1 M, 10 mL) and brine (10 mL)
  3. extractionThe aqueous layers were extracted with ethyl acetate (10 mL)
  4. dry with materialthe combined organic layers were dried over sodium sulfate
  5. customPurification by chromatography (SiO2, heptane:ethyl acetate=30:70 to 0:100)

Sources & evidence

ORD record
ord-071093e12191444abeeb0d85d2fcabe0
Source dataset
uspto-grants-2013_03
Patent number
US08404679B2

Reaction notes

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