Methanol → cis-N-(2-{[7-[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 82860Notes

Reaction equation

HRID 82860 reaction equation
O=[C:2]1[N:7]([C@H:8]2[C@@H:17]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])[C:16]3[CH:15]=[C:14]([O:26][CH2:27][CH2:28][NH:29][S:30]([C:33]4[N:34]=[CH:35][N:36]([CH3:38])[CH:37]=4)(=[O:32])=[O:31])[CH:13]=[CH:12][C:11]=3[CH2:10][CH2:9]2)[C:6](=O)[CH:5]2[CH:3]1[CH2:4]2.CO>O1CCCC1.ClCCl>[CH:5]12[CH2:4][CH:3]1[CH2:2][N:7]([C@H:8]1[C@@H:17]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])[C:16]3[CH:15]=[C:14]([O:26][CH2:27][CH2:28][NH:29][S:30]([C:33]4[N:34]=[CH:35][N:36]([CH3:38])[CH:37]=4)(=[O:32])=[O:31])[CH:13]=[CH:12][C:11]=3[CH2:10][CH2:9]1)[CH2:6]2

Participants

5

Reactant 2

HCID 887MethanolHCID 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

Product 1

HCID 86685679cis-N-(2-{[7-[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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

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 (38 mg, 0.069 mmol) was dissolved in tetrahydrofuran (2 mL) and borane tetrahydrofuran complex was added (1 N, 0.4 mL, 0.4 mmol). The reaction mixture was heated to 50° C. for 3.5 h. After cooling to room temperature methanol (0.2 mL) was added dropwise and stirring was continued for 30 min. The reaction mixture was diluted with dichloromethane, washed with saturated sodium chloride solution and dried (magnesium sulfate). The solvent was evaporated in vacuo and the crude product was purified by flash chromatography (silica, dichloromethane/methanol). Yield: 4 mg (7.6 μmol, 11%, colorless oil).

Workup

  1. additionborane tetrahydrofuran complex was added (1 N, 0.4 mL, 0.4 mmol)
  2. additionwas added dropwise
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried (magnesium sulfate)
  5. customThe solvent was evaporated in vacuo
  6. customthe crude product was purified by flash chromatography (silica, dichloromethane/methanol)

Sources & evidence

ORD record
ord-0c522fa8dbc34f79bc0b37a6eee55150
Source dataset
uspto-grants-2014_09
Patent number
US08846741B2

Reaction notes

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