Triethylamine → HCID 58951395, compound

HRID 1445829Notes

Reaction equation

HRID 1445829 reaction equation
CS(Cl)(=O)=O.[CH3:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[O:23][C:24]([CH3:30])=[C:25]([CH2:27][CH2:28]O)[N:26]=3)=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)(=[O:9])=[O:8].C(N(CC)CC)C.[CH3:38][NH:39][CH:40]([CH3:42])[CH3:41]>ClCCl.O1CCCC1>[CH:40]([N:39]([CH2:28][CH2:27][C:25]1[N:26]=[C:22]([C:19]2[CH:18]=[CH:17][C:16]([C:13]3[CH:12]=[CH:11][C:10]([S:7]([CH3:6])(=[O:9])=[O:8])=[CH:15][CH:14]=3)=[CH:21][CH:20]=2)[O:23][C:24]=1[CH3:30])[CH3:38])([CH3:42])[CH3:41]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 78485N-MethylisopropylamineHCID 58951415HCID 58951415, compound

Product 1

HCID 58951395HCID 58951395, compoundYield 18.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add methanesulfonyl chloride (0.135 g, 0.935 mmol) to a cool (0° C.) solution of 2-[2-(4′-methanesulfonyl-biphenyl-4-yl)-5-methyl-oxazol-4-yl]-ethanol (0.257 g, 0.719 mmol) and triethylamine (0.182 g, 1.80 mmol) in dichloromethane (5 mL). Warm to room temperature and stir for 1 hour. Remove the solvents, transfer the residue to a sealed tube, add tetrahydrofuran (5 mL) and N-methyl-isopropylamine (0.526 g, 7.19 mmol), and heat at 60° C. overnight. Add dichloromethane and wash the crude organic material with saturated sodium chloride solution. Dry the organic layer over Na2SO4, filter, and concentrate. Purify on silica gel eluting with 5% ammoniated methanol in dichloromethane to give isopropyl-{2-[2-(4′-methanesulfonyl-biphenyl-4-yl)-5-methyl-oxazol-4-yl]-ethyl}-methyl-amine (0.056 g, 18%): mass spectrum (m/e): 413 (M+1). Treat the recovered material (0.056 g, 0.131 mmol) with 1N HCl (144 μL, 0.144 mmol) in ether, concentrate, and lyophilize to give the title compound (12.8 mg): MS (m/e): 413 (M+1).

Workup

  1. customRemove the solvents
  2. temperatureheat at 60° C. overnight
  3. washAdd dichloromethane and wash the crude organic material with saturated sodium chloride solution
  4. dry with materialDry the organic layer over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify on silica gel eluting with 5% ammoniated methanol in dichloromethane

Sources & evidence

ORD record
ord-7c762489199f4b4891c30f60c6be740c
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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