Water → HCID 86642498, compound

HRID 1631959Notes

Reaction equation

HRID 1631959 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.[C:13]([C:15]1[CH:16]=[CH:17][C:18]2[NH:22][C:21](=[O:23])[N:20]([CH:24]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:19]=2[CH:38]=1)#[N:14].C(N(CC)CC)C.O>CN(C1C=CN=CC=1)C.O1CCCC1>[C:28]([O:27][C:25](=[O:26])[CH:24]([N:20]1[C:19]2[CH:38]=[C:15]([C:13]#[N:14])[CH:16]=[CH:17][C:18]=2[N:22]([S:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)(=[O:11])=[O:10])[C:21]1=[O:23])[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)([CH3:31])([CH3:29])[CH3:30]

Participants

7

Reactant 4

HCID 962WaterHCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 86642497tert-Butyl (6-cyano-2-oxo-2,3-dihydrobenzimidazol-1-yl)phenylacetate

Product 1

HCID 86642498HCID 86642498, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1.63 g (7.87 mmol) of 4-methoxybenzenesulfonyl chloride were added to a solution of 2.50 g (7.16 mmol) of tert-butyl (6-cyano-2-oxo-2,3-dihydro-benzimidazol-1-yl)phenylacetate (XIc), 1.98 ml (14.3 mmol) of triethylamine and a catalytic amount of DMAP in tetrahydrofuran (60 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 10-40% ethyl acetate in cyclohexane). Yield: 2.90 g (78%) of colorless solid

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 10-40% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-9b978b9becff4cc494a242dd3053980b
Source dataset
uspto-grants-2014_07
Patent number
US08791148B2

Reaction notes

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