Acetic Acid → HCID 178490790, compound

HRID 1913127Notes

Reaction equation

HRID 1913127 reaction equation
C(S[C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][N:15]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[C:16]2=[O:19])=[CH:11][C:10]=1[O:29][C@@H:30]1[CH2:35][CH2:34][C@H:33]([NH:36][C:37](=[O:39])[CH3:38])[CH2:32][CH2:31]1)C1C=CC=CC=1.C(O)(=O)C.O.[S:45]([Cl:49])(Cl)(=[O:47])=[O:46].[Cl:50]CCl>C(OCC)(=O)C>[C:37]([NH:36][C@@H:33]1[CH2:34][CH2:35][C@H:30]([O:29][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][C:9]=2[S:45]([Cl:49])(=[O:47])=[O:46])[C:16](=[O:19])[N:15]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[CH:14]=[C:13]3[Cl:50])[CH2:31][CH2:32]1)(=[O:39])[CH3:38]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 962WaterHCID 6344DichloromethaneHCID 24648Sulfuryl chlorideHCID 178490768HCID 178490768, compound

Product 1

HCID 178490790HCID 178490790, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

37 mg of N-{4-[7-benzylsulfanyl-2-(4-methoxy-benzyl)-1-oxo-1,2-dihydro-isoquinolin-6-yloxy]-cyclohexyl}-acetamide (128, crude product) were dissolved in 5 ml of dichloromethane. At 0° C., 16.4 mg (0.273 mmol) of acetic acid, 4.9 mg (0.273 mmol) of water and 273 μl (0.273 mmol) of sulfuryl chloride (1 M in dichloromethane) were added. After 30 minutes, ethyl acetate was added and the solution was washed with sodium bicarbonate solution (2%), water and saturated sodium chloride solution. The organic layer was dried with Na2SO4 and evaporated. The so obtained crude product was used without further purification. Rt=1.55 min (Method C). Detected mass: 553.5 (M+H+).

Workup

  1. washthe solution was washed with sodium bicarbonate solution (2%), water and saturated sodium chloride solution
  2. dry with materialThe organic layer was dried with Na2SO4
  3. customevaporated
  4. customThe so obtained crude product
  5. customwas used without further purification

Sources & evidence

ORD record
ord-b5882072e16a471e90bb7c3ebd6f1177
Source dataset
uspto-grants-2013_12
Patent number
US08609691B2

Reaction notes

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