Diisopropylethylamine → HCID 178468179, compound

HRID 1914656Notes

Reaction equation

HRID 1914656 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:3]=1[C:4]([NH:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([C@@H:13]([OH:15])[CH3:14])[CH2:9][CH2:8]1)=[O:5].CCN(C(C)C)C(C)C>C(Cl)Cl.CS(C)=O>[C:13]([C@H:10]1[CH2:11][CH2:12][C@H:7]([NH:6][C:4](=[O:5])[C:3]2[CH:16]=[C:17]([C:20]([F:21])([F:22])[F:23])[CH:18]=[CH:19][C:2]=2[Cl:1])[CH2:8][CH2:9]1)(=[O:15])[CH3:14]

Participants

5

Reactant 2

HCID 81531Diisopropylethylamine2×HCID 178462274HCID 178462274, compound

Product 1

HCID 178468179HCID 178468179, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of Trans-2-chloro-N-(−4-((S)-1-hydroxyethyl)-cyclohexyl)-5-(trifluoromethyl)benzamide (1.00 g, 2.86 mmol) in DCM (20 mL) is added DIPEA (1.48 g, 11.4 mmol) of DIPEA. The reaction mixture is cooled to 0° C. and then a solution of sulfur trioxide-pyridine complex (1.82 g, 11.4 mmol) in DMSO (5 mL) is added. The reaction mixture is stirred at 0° C. for 10 min and then partitioned between DCM and water. The organic phase was washed with water and brine, dried over MgSO4, filtered and the solvent was removed in vacuo. Purification by chromatography on a pre-packed 40 g silica gel column using 0-100% EtOAc in isohexane (gradient elution) gave the desired product as a colourless solid.

Workup

  1. custompartitioned between DCM and water
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo
  6. customPurification by chromatography on a pre-packed 40 g silica gel column

Sources & evidence

ORD record
ord-b65e66248f2d4619937e08a904b5a837
Source dataset
uspto-grants-2013_12
Patent number
US08614213B2

Reaction notes

Loading…