Dimethylformamide → {4-[2-(4-Methanesulfonyl-phenyl)-6-methoxy-naphthalen-1-yloxy]-phenyl}-(2-piperidin-1-yl-ethyl)-carbamic acid tert-butyl ester

HRID 732785Notes

Reaction equation

HRID 732785 reaction equation
[C:1]([O:5][C:6](=[O:37])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[C:24]3[C:19](=[CH:20][C:21]([O:25][CH3:26])=[CH:22][CH:23]=3)[CH:18]=[CH:17][C:16]=2[C:27]2[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][CH:28]=2)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:40][C:41](C)([O-])[CH3:42].[K+].Cl[CH2:47]Cl.[CH3:49][N:50]([CH3:53])[CH:51]=O>>[C:1]([O:5][C:6](=[O:37])[N:7]([C:8]1[CH:9]=[CH:10][C:11]([O:14][C:15]2[C:24]3[C:19](=[CH:20][C:21]([O:25][CH3:26])=[CH:22][CH:23]=3)[CH:18]=[CH:17][C:16]=2[C:27]2[CH:28]=[CH:29][C:30]([S:33]([CH3:36])(=[O:34])=[O:35])=[CH:31][CH:32]=2)=[CH:12][CH:13]=1)[CH2:47][CH2:49][N:50]1[CH2:53][CH2:42][CH2:41][CH2:40][CH2:51]1)([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 24758Sodium hydrideHCID 23665647Potassium tert-butoxideHCID 68519035{4-[2-(4-Methanesulfonyl-phenyl)-6-methoxy-naphthalen-1-yloxy]-phenyl}-carbamic acid tert-butyl ester

Product 1

HCID 59751432{4-[2-(4-Methanesulfonyl-phenyl)-6-methoxy-naphthalen-1-yloxy]-phenyl}-(2-piperidin-1-yl-ethyl)-carbamic acid tert-butyl esterYield 50%

Procedure

Heat a solution of {4-[2-(4-methanesulfonyl-phenyl)-6-methoxy-naphthalen-1-yloxy]-phenyl}-carbamic acid tert-butyl ester (200 mg, 0.38 mmol), 2-chloroethyl-1-piperidine hydrochloride (100 mg, 0.57 mmol) and 60% sodium hydride (38 mg, 0.94 mmol) in N,N-dimethylformamide to 60° C. and stir for 18 hours. Add potassium tert-butoxide (760 mg, 0.67 mmol) and 2-chloroethyl-1-piperidine hydrochloride (46 mg, 0.25 mmol) and stir for an additional 2 hours, then cool to ambient temperature. Dilute the reaction with dichloromethane, wash with saturated sodium bicarbonate, dry with magnesium sulfate and chromatograph on silica gel with dichloromethane/methanol mixtures to give 120 mg of the title compound (50%). Mass spectrum (ion spray): m/z=631.3 (M+H).

Workup

  1. additionDilute
  2. washwash with saturated sodium bicarbonate
  3. dry with materialdry with magnesium sulfate and chromatograph on silica gel with dichloromethane/methanol

Sources & evidence

ORD record
ord-deba28ea807c49ca918fe50f44c5f376
Source dataset
uspto-grants-2009_09
Patent number
US07585977B2

Reaction notes

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