Diisopropylethylamine → HCID 178520977, compound

HRID 1914653Notes

Reaction equation

HRID 1914653 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:3]=1[C:4]([NH:6][C@H:7]1[CH2:12][CH2:11][C@@H:10]([CH2:13][OH:14])[CH2:9][CH2:8]1)=[O:5].CCN(C(C)C)C(C)C.C1C=CN=CC=1.O=S(=O)=O>C(Cl)Cl.CS(C)=O>[Cl:1][C:2]1[CH:18]=[CH:17][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:15][C:3]=1[C:4]([NH:6][C@H:7]1[CH2:12][CH2:11][C@@H:10]([CH:13]=[O:14])[CH2:9][CH2:8]1)=[O:5]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 168533Sulfur trioxide-pyridineHCID 178523766HCID 178523766, compound

Product 1

HCID 178520977HCID 178520977, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of Cis-2-chloro-N-(−4-(hydroxymethyl)cyclohexyl)-5-(trifluoromethyl)-benzamide (1 g, 2.98 mmol) in DCM (18 mL) is added DIPEA (2.081 mL, 11.91 mmol). The reaction mixture is cooled to 0° C. and pyridine-sulfur trioxide (1.896 g, 11.91 mmol) in DMSO (6 mL) is added. The reaction mixture is stirred at this temperature for 30 mins. The reaction mixture is partitioned between water and DCM and passed through a phase separator. The DCM layer was collected and concentrated under reduced pressure to give a colourless oil. Purification by chromatography on a pre-packed silica gel column using 0-100% EtOAc in isohexane gradient elution gave the desired product as a colourless solid.

Workup

  1. customThe reaction mixture is partitioned between water and DCM
  2. customThe DCM layer was collected
  3. concentrationconcentrated under reduced pressure
  4. customto give a colourless oil
  5. customPurification by chromatography on a pre-packed silica gel column
  6. wash0-100% EtOAc in isohexane gradient elution

Sources & evidence

ORD record
ord-b0ae024fb81949c983bb095d68318113
Source dataset
uspto-grants-2013_12
Patent number
US08614213B2

Reaction notes

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