2-(3-Bromopropoxy)tetrahydro-2H-pyran → HCID 25168389, compound

HRID 1510335Notes

Reaction equation

HRID 1510335 reaction equation
[S:1]1[CH2:5][CH2:4][N:3]=[C:2]1[NH:6][CH:7]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:18]=1[Cl:24])[CH2:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([CH3:16])[CH:10]=1.C([O-])(C)(C)C.[K+].Br[CH2:32][CH2:33][CH2:34][O:35][CH:36]1[CH2:41][CH2:40][CH2:39][CH2:38][O:37]1>O1CCCC1>[O:37]1[CH2:38][CH2:39][CH2:40][CH2:41][CH:36]1[O:35][CH2:34][CH2:33][CH2:32][N:3]1[CH2:4][CH2:5][S:1][C:2]1=[N:6][CH:7]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:18]=1[Cl:24])[CH2:8][C:9]1[CH:10]=[C:11]([CH3:16])[CH:12]=[C:13]([CH3:15])[CH:14]=1

Participants

5

Reactant 3

HCID 27779882-(3-Bromopropoxy)tetrahydro-2H-pyranHCID 23665647Potassium tert-butoxideHCID 25002901HCID 25002901, compound

Product 1

HCID 25168389HCID 25168389, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(4,5-dihydrothiazol-2-yl)amino-1-(2,3-dichlorophenyl)-2-(3,5-dimethylphenyl)-ethane (300 mg), potassium tert.-butanolate and tetrahydrofuran (THF, 10 ml) was treated at room temperature with 2-(3-bromo-propoxy)-tetrahydropyran (210 mg) for 3 days. Aqueous work-up by dilution in ethyl acetate, washing with an aqueous potassium carbonate solution (5% strength) and water and drying over sodium sulphate yielded a crude product that was purified by column chromatography over silica gel to give 200 mg of the title compound.

Workup

  1. washAqueous work-up by dilution in ethyl acetate, washing with an aqueous potassium carbonate solution (5% strength) and water
  2. dry with materialdrying over sodium sulphate
  3. customyielded a crude product that
  4. customwas purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-8dae74fc22a143d2953e9035ba888ec3
Source dataset
uspto-grants-2012_07
Patent number
US08211924B2

Reaction notes

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