Acetyl chloride → cis-N-(2-{[7-(2,4-Dioxo-3-azabicyclo[3.1.0]hex-3-yl)-8-(2-fluorobenzyl)-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}ethyl)-1-methyl-1H-imidazole-4-sulfonamide

HRID 82859Notes

Reaction equation

HRID 82859 reaction equation
[NH2:1][C@H:2]1[C@@H:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])[C:10]2[CH:9]=[C:8]([O:20][CH2:21][CH2:22][NH:23][S:24]([C:27]3[N:28]=[CH:29][N:30]([CH3:32])[CH:31]=3)(=[O:26])=[O:25])[CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1.[C:33](Cl)(=[O:35])[CH3:34]>>[O:35]=[C:33]1[N:1]([C@H:2]2[C@@H:11]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])[C:10]3[CH:9]=[C:8]([O:20][CH2:21][CH2:22][NH:23][S:24]([C:27]4[N:28]=[CH:29][N:30]([CH3:32])[CH:31]=4)(=[O:26])=[O:25])[CH:7]=[CH:6][C:5]=3[CH2:4][CH2:3]2)[C:8](=[O:20])[CH:7]2[CH:34]1[CH2:6]2

Participants

3

Reactant 2

HCID 6367Acetyl chlorideHCID 86685677cis-N-(2-{[7-Amino-8-(2-fluorobenzyl)-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}ethyl)-1-methyl-1H-imidazole-4-sulfonamide

Product 1

HCID 86685678cis-N-(2-{[7-(2,4-Dioxo-3-azabicyclo[3.1.0]hex-3-yl)-8-(2-fluorobenzyl)-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}ethyl)-1-methyl-1H-imidazole-4-sulfonamide

Procedure

cis-N-(2-{[7-Amino-8-(2-fluorobenzyl)-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}ethyl)-1-methyl-1H-imidazole-4-sulfonamide (60 mg, 0.105 mmol) in acetyl chloride (2 mL, 28.1 mmol) was heated under reflux for 30 min. The acetyl chloride was evaporated in vacuo. The crude product dissolved in dichloromethane and washed successively with saturated sodium bicarbonate and saturated sodium chloride and dried (magnesium sulfate). The crude product was used for next step without further purification. Yield: 38 mg (colorless foam).

Workup

  1. temperatureunder reflux for 30 min
  2. customThe acetyl chloride was evaporated in vacuo
  3. dissolutionThe crude product dissolved in dichloromethane
  4. washwashed successively with saturated sodium bicarbonate and saturated sodium chloride
  5. dry with materialdried (magnesium sulfate)
  6. customThe crude product was used for next step without further purification

Sources & evidence

ORD record
ord-fbbac4f7787b491abee8ea639e3c4434
Source dataset
uspto-grants-2014_09
Patent number
US08846741B2

Reaction notes

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