2-Propanesulfonyl chloride → HCID 11525901, compound

HRID 899161Notes

Reaction equation

HRID 899161 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][N:11]1[CH2:18][CH:17]2[O:19][CH:13]([CH2:14][N:15]([CH2:20][C:21]3[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=3)[CH2:16]2)[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:29]([S:32](Cl)(=[O:34])=[O:33])([CH3:31])[CH3:30]>C(Cl)Cl>[CH2:1]([N:8]([CH2:9][CH2:10][N:11]1[CH2:12][CH:13]2[O:19][CH:17]([CH2:16][N:15]([CH2:20][C:21]3[CH:22]=[CH:23][C:24]([C:25]#[N:26])=[CH:27][CH:28]=3)[CH2:14]2)[CH2:18]1)[S:32]([CH:29]([CH3:31])[CH3:30])(=[O:34])=[O:33])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 824082-Propanesulfonyl chlorideHCID 69071248HCID 69071248, compound

Product 1

HCID 11525901HCID 11525901, compoundYield 43.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[7-(2-Benzylamino-ethyl)-9-oxa-3,7-diaza-bicyclo[3.3.1]non-3-ylmethyl]-benzonitrile (0.5 g, 1.33 mmol, from step (iii) above) was taken in 30 ml of DCM/10% aq. NaHCO3 (1:1) and stirred for 15 min. Isopropane sulfonyl chloride (0.28 g, 1.99 mmol) was added and stirring continued at RT for 1.5 h. The organic layer was separated, washed with brine and dried over sodium sulfate. Solvent evaporation under reduced pressure followed by purification over silica gel using 10% ethyl acetate in petroleum ether as eluent afforded the desired product (280 mg) as white solid. This was further purified by prep HPLC (0.1% TFA in acetonitrile), evaporated under reduced pressure, and the residue was partitioned between sat NaHCO3 and DCM. The organic layer was washed with brine and dried over sodium sulfate. Solvent evaporation under reduced pressure afforded the title compound (140 mg) as an off-white solid.

Workup

  1. stirringstirring
  2. waitcontinued at RT for 1.5 h
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. customSolvent evaporation under reduced pressure
  7. customfollowed by purification over silica gel using 10% ethyl acetate in petroleum ether as eluent

Sources & evidence

ORD record
ord-d556fd8c1a3b4353b27724de54d466e5
Source dataset
uspto-grants-2008_04
Patent number
US07354917B2

Reaction notes

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