HCID 178513943, compound → HCID 178511247, compound

HRID 1984921Notes

Reaction equation

HRID 1984921 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][C@H:13]2[CH2:18][CH2:17][C@H:16]([C:19]([NH2:21])=O)[CH2:15][CH2:14]2)(=[O:10])=[O:9])=[C:4]([O:22][C:23]([F:26])([F:25])[F:24])[CH:3]=1>C1COCC1>[NH2:21][CH2:19][C@H:16]1[CH2:15][CH2:14][C@H:13]([CH2:12][NH:11][S:8]([C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=2[O:22][C:23]([F:25])([F:26])[F:24])(=[O:10])=[O:9])[CH2:18][CH2:17]1

Participants

3

Reactant 1

HCID 178513943HCID 178513943, compound

Product 1

HCID 178511247HCID 178511247, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of trans-4-[(4-bromo-2-trifluoromethoxy-benzenesulfonylamino)-methyl]-cyclohexanecarboxylic acid amide (4.2 g, 9.2 mmol) in THF (40 mL) was added a solution of 1 M BH3 in THF (32 mL, 32 mmol) over 40 min. The mixture was refluxed for 2 hr. After cooling to 0° C., the mixture was quenched with water (7 mL). To the resulting mixture were added 4 M HCl in EtOAc (28 mL) and MeOH (28 mL) and the mixture was concentrated. To the residue was added MeOH (28 mL) and the mixture was once again concentrated. The resulting HCl-salt was recrystallized from Et2O and subsequently neutralized with 1 M aqueous sodium hydroxide. The aqueous layer was extracted with CH2Cl2 (twice), the organic layers combined, dried over sodium sulfate, and concentrated under reduced pressure to give trans-N-(4-aminomethyl-cyclohexylmethyl)-4-bromo-2-trifluoromethoxy-benzenesulfonamide as a white solid (3.0 g, 74%).

Workup

  1. temperatureThe mixture was refluxed for 2 hr
  2. customthe mixture was quenched with water (7 mL)
  3. additionTo the resulting mixture were added 4 M HCl in EtOAc (28 mL) and MeOH (28 mL)
  4. concentrationthe mixture was concentrated
  5. additionTo the residue was added MeOH (28 mL)
  6. concentrationthe mixture was once again concentrated
  7. customThe resulting HCl-salt was recrystallized from Et2O
  8. extractionThe aqueous layer was extracted with CH2Cl2 (twice), the organic layers
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-010a9ea5db1740ab873f9741d622711a
Source dataset
uspto-grants-2009_06
Patent number
US07544690B2

Reaction notes

Loading…