Water → HCID 66755192, compound

HRID 1643969Notes

Reaction equation

HRID 1643969 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[Cl:13][C:14]1[CH:15]=[CH:16][C:17]2[NH:21][C:20](=[O:22])[N:19]([CH:23]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[C:24]([N:26]3[CH2:31][CH2:30][N:29]([CH:32]4[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][CH2:33]4)[CH2:28][CH2:27]3)=[O:25])[C:18]=2[CH:51]=1.C(N(CC)CC)C.O>CN(C1C=CN=CC=1)C.O1CCCC1>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]2[N:21]([S:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)(=[O:11])=[O:10])[C:20](=[O:22])[N:19]([CH:23]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[C:24]([N:26]3[CH2:31][CH2:30][N:29]([CH:32]4[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][CH2:33]4)[CH2:28][CH2:27]3)=[O:25])[C:18]=2[CH:51]=1

Participants

7

Reactant 4

HCID 962WaterHCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 66754935HCID 66754935, compound

Product 1

HCID 66755192HCID 66755192, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

167 mg (0.81 mmol) of 4-methoxybenzenesulfonyl chloride were added to a solution of 460 mg (0.73 mmol) of tert-butyl 4-{-4-[2-(6-chloro-2-oxo-2,3-dihydrobenzimidazol-1-yl)-2-phenylacetyl]-piperazin-1-yl}piperidin-1-carboxylate (XIIIa), 0.21 ml (1.47 mmol) of triethylamine and a catalytic amount of DMAP in tetrahydrofuran (8 ml) while stirring at room temperature, and the mixture was then stirred at room temperature for 16 h. The reaction solution was mixed with water and extracted with ethyl acetate (3×60 ml). The combined organic phases were washed with water and saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (mobile phase gradient 5-10% methanol in dichloromethane). Yield: 517 g (97%) of colorless oil

Workup

  1. extractionextracted with ethyl acetate (3×60 ml)
  2. washThe combined organic phases were washed with water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by chromatography on silica gel (mobile phase gradient 5-10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-718fc101107a46e9957e97cf1d99643c
Source dataset
uspto-grants-2012_02
Patent number
US08119676B2

Reaction notes

Loading…