4-Toluenesulfonyl chloride → HCID 178427789, compound

HRID 2361667Notes

Reaction equation

HRID 2361667 reaction equation
[CH:1]1([N:5]2[CH2:11][CH2:10][CH2:9][N:8]([C:12]([C@@H:14]3[CH2:17][C@H:16]([OH:18])[CH2:15]3)=[O:13])[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:26]1([CH3:36])[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1>C(Cl)Cl>[CH3:36][C:26]1[CH:31]=[CH:30][C:29]([S:32]([O:18][C@H:16]2[CH2:17][C@@H:14]([C:12]([N:8]3[CH2:9][CH2:10][CH2:11][N:5]([CH:1]4[CH2:4][CH2:3][CH2:2]4)[CH2:6][CH2:7]3)=[O:13])[CH2:15]2)(=[O:34])=[O:33])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 178521040HCID 178521040, compound

Product 1

HCID 178427789HCID 178427789, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of cis-3-[(4-cyclobutyl-1,4-diazepan-1-yl)carbonyl]cyclobutanol (50 mg, 0.19 mmol) in DCM (2 ml) at RT was added triethylamine (77 mg, 0.7 mmol) and toluene-4-sulfonyl chloride (108 mg, 0.57 mmol). The mixture was stirred at RT for 1 h and then at 35° C. for 2 h. After cooling to RT and dilution with DCM the mixture was washed with 1:1 H2O/saturated NaHCO3. The organic layer was dried (Na2SO4), filtered and concentrated at reduced pressure. Purification by silica FCC (eluting with DCM/MeOH/NH3 90:10:1) provided the title compound as colourless oil (73 mg, 91%).

Workup

  1. waitat 35° C. for 2 h
  2. temperatureAfter cooling to RT
  3. washdilution with DCM the mixture was washed with 1:1 H2O/saturated NaHCO3
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated at reduced pressure
  7. customPurification
  8. washby silica FCC (eluting with DCM/MeOH/NH3 90:10:1)

Sources & evidence

ORD record
ord-c324a96462c24444b6c856524546fa87
Source dataset
uspto-grants-2014_04
Patent number
US08691804B2

Reaction notes

Loading…