Triethylamine → HCID 58561925, compound

HRID 2167353Notes

Reaction equation

HRID 2167353 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]([NH:5][CH2:6][C:7]1([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:4].CCN(CC)CC.[CH:28]1([CH2:31][S:32](Cl)(=[O:34])=[O:33])[CH2:30][CH2:29]1>C(Cl)Cl>[CH:28]1([CH2:31][S:32]([N:16]2[CH2:17][CH2:18][N:13]([C:7]3([CH2:6][NH:5][C:3](=[O:4])[C:2]([F:19])([F:1])[F:20])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]3)[CH2:14][CH2:15]2)(=[O:34])=[O:33])[CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 14106996Cyclopropylmethanesulphonyl chlorideHCID 58561808HCID 58561808, compound

Product 1

HCID 58561925HCID 58561925, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring ice-cold solution of 14 (10.0 g, 34.09 mmol) and Et3N (14.2 mL, 102.27 mmol) in CH2Cl2 (200 mL) was slowly added 1-cyclopropylmethylsulfonyl chloride (5.27 g, 34.09 mmol). The mixture stirred at ambient temperature under an atmosphere of nitrogen for 3 h. The mixture was washed with 2 N NaOH (50 mL), 2 N HCl (50 mL), H2O (50 mL), brine (50 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to afford N-((1-(4-(cyclopropylmethylsulfonyl)piperazin-1-yl)cyclohexyl)methyl)-2,2,2-trifluoroacetamide (18) as an off-white solid (14.00 g, quantitative): MS (ESI+) m/z 412.

Workup

  1. washThe mixture was washed with 2 N NaOH (50 mL), 2 N HCl (50 mL), H2O (50 mL), brine (50 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-44ae1b9179fa4e1b938a86751c3d3d47
Source dataset
uspto-grants-2015_06
Patent number
US09045445B2

Reaction notes

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