Iodoethane → HCID 69217996, compound

HRID 1393112Notes

Reaction equation

HRID 1393112 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9](=[O:37])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][CH2:19][C:20]2[S:24][C:23]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)=[N:22][C:21]=2[CH3:35])=[CH:14][C:13]=1[CH3:36].I[CH2:39][CH3:40]>CS(C)=O.CCOCC>[CH3:7][O:8][C:9](=[O:37])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]([CH2:39][CH3:40])[CH2:19][C:20]2[S:24][C:23]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:32])[F:33])=[CH:27][CH:26]=3)=[N:22][C:21]=2[CH3:35])=[CH:14][C:13]=1[CH3:36]

Participants

6

Reactant 3

HCID 6340Iodoethane2×HCID 11430Potassium CarbonateHCID 69220462HCID 69220462, compound

Product 1

HCID 69217996HCID 69217996, compoundYield 58.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

A suspension of potassium carbonate (76 mg, 0.55 mmol), and (2-methyl-4-{[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenoxy)-acetic acid methyl ester (225 mg, 0.50 mmol, example 18.2) in DMSO (3 ml) was treated with iodoethane (0.04 ml, 0.53 mmol) in DMSO (0.5 ml) and stirred for 19 h at RT. Again iodoethane (0.34 ml, 4.20 mmol) in 2 portions over 7 h was added. The reaction mixture was taken up in ether and washed with KHSO4-solution (10%). The organic phase was washed with NaCl (10%), dried (Na2SO4) and evaporated. Purification by flash chromatography (SiO2, n-heptane/AcOEt=9/1) gave 141 mg of pure (4-{ethyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-2-methyl-phenoxy)-acetic acid methyl ester, MS: 479.5 (MH)+.

Workup

  1. washwashed with KHSO4-solution (10%)
  2. washThe organic phase was washed with NaCl (10%)
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customPurification by flash chromatography (SiO2, n-heptane/AcOEt=9/1)

Sources & evidence

ORD record
ord-2375bca6b2094e99bd85ca73eaf497fc
Source dataset
uspto-grants-2008_03
Patent number
US07345067B2

Reaction notes

Loading…