Diisopropylethylamine → HCID 16731373, compound

HRID 507342Notes

Reaction equation

HRID 507342 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[C:4]([O:14][CH2:15][CH:16]([OH:24])[CH2:17][N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.[F:34][C:35]([F:47])([F:46])[C:36]1[CH:37]=[C:38]([S:42](Cl)(=[O:44])=[O:43])[CH:39]=[CH:40][CH:41]=1>CN(C=O)C.C(OCC)(=O)C>[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[C:4]([O:14][CH2:15][CH:16]([OH:24])[CH2:17][N:18]2[CH2:23][CH2:22][N:21]([S:42]([C:38]3[CH:39]=[CH:40][CH:41]=[C:36]([C:35]([F:34])([F:46])[F:47])[CH:37]=3)(=[O:44])=[O:43])[CH2:20][CH2:19]2)=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 27332503-(Trifluoromethyl)benzenesulfonyl chlorideHCID 167304831-(9H-carbazol-4-yloxy)-3-piperazin-1-ylpropan-2-ol

Product 1

HCID 16731373HCID 16731373, compoundYield 31.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(9H-carbazol-4-yloxy)-3-piperazin-1-ylpropan-2-ol (0.2 g, 0.614 mmol) in DMF (4 mL), was added DIPEA (0.05 mL, 0.301 mmol) followed by the drop-wise addition of 3-trifluoromethylbenzenesulfonyl chloride (0.098 g, 0.61 mmol) at room temperature and the reaction mixture was stirred for 3 hours. Subsequently the reaction mixture was diluted with ethyl acetate (30 mL), washed with water and brine solution. The organic layer was dried on anhydrous Na2SO4, concentrated, and purified by precipitating the compound from dichloromethane by adding hexane, to give the required compound as a pale yellow colored solid (0.102 g, 30% yield). 1H NMR (400 MHz, DMSO): δ 2.30-2.90 (m, 6H), 3.00-3.30 (m, 4H), 4.00-4.30 (m, 4H), 5.00 (s, 1H), 6.61 (d, 1H, J=8 Hz), 7.00-7.20 (m, 2H), 7.25-7.40 (m, 2H), 7.42 (d, 1H, J=8.0 Hz), 7.80-8.00 (m, 2H), 8.06 (d, 1H, J=8 Hz), 8.20-8.30 (m, 2H), 11.26 (d, 1H, J=12 Hz). MS m/z: 534.1 (M+1).

Workup

  1. washwashed with water and brine solution
  2. dry with materialThe organic layer was dried on anhydrous Na2SO4
  3. concentrationconcentrated
  4. custompurified
  5. customby precipitating the compound from dichloromethane
  6. additionby adding hexane

Sources & evidence

ORD record
ord-2c394b8e1efe4d86b5001f9f922479c5
Source dataset
uspto-grants-2010_08
Patent number
US07786142B2

Reaction notes

Loading…