Triethylamine → HCID 178429124, compound

HRID 237496Notes

Reaction equation

HRID 237496 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Br:6][C:7]1[C:18]([CH3:19])=[CH:17][C:10]([O:11][C@@H:12]2[CH2:15][C@H:14]([NH2:16])[CH2:13]2)=[CH:9][C:8]=1[CH3:20].C(N(CC)CC)C>ClCCl>[Br:6][C:7]1[C:18]([CH3:19])=[CH:17][C:10]([O:11][C@@H:12]2[CH2:15][C@H:14]([NH:16][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:13]2)=[CH:9][C:8]=1[CH3:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178429121HCID 178429121, compound

Product 1

HCID 178429124HCID 178429124, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methanesulfonyl chloride (0.16 mL), cis-3-(4-Bromo-3,5-dimethylphenoxy)cyclobutanamine (300 mg) and triethylamine (0.3 mL) are stirred at 0° C. in dry dichloromethane (25 mL). After 10 min, the reaction mixture is warmed to ambient temperature. After stirring for 3 hours, the mixture is diluted with dichloromethane, washed with 10% aqueous solution of KHSO4, then with 10% aqueous solution of K2CO3. The organic phase was passed through a phase separator and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 90:10→50:50) to give the title compound. Yield: 200 mg.

Workup

  1. washwashed with 10% aqueous solution of KHSO4
  2. concentrationconcentrated
  3. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 90:10→50:50)

Sources & evidence

ORD record
ord-4d5b9699741845b8b26dabab90bdf4e4
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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