2-Chlorocyclohexanone → ethyl ((1S)-5-{3-[2-methoxy-4-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)phenoxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate

HRID 2235898Notes

Reaction equation

HRID 2235898 reaction equation
[NH2:1][C:2]([C:4]1[CH:29]=[CH:28][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[C@H:18]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:17][CH2:16]3)=[C:6]([O:30][CH3:31])[CH:5]=1)=[S:3].Cl[CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][C:34]1=O>CCO>[CH3:31][O:30][C:6]1[CH:5]=[C:4]([C:2]2[S:3][C:33]3[CH2:38][CH2:37][CH2:36][CH2:35][C:34]=3[N:1]=2)[CH:29]=[CH:28][C:7]=1[O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[C@H:18]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:17][CH2:16]2

Participants

4

Reactant 2

HCID 132032-ChlorocyclohexanoneHCID 16110447ethyl ((1S)-5-{3-[4-(aminocarbonothioyl)-2-methoxyphenoxy]propoxy)-2,3-dihydro-1H-inden-1-yl)acetate

Product 1

HCID 16110464ethyl ((1S)-5-{3-[2-methoxy-4-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)phenoxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetateYield 59.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl ((1S)-5-{3-[4-(aminocarbonothioyl)-2-methoxyphenoxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate (Example 146, 90 mg, 0.2 mmol) and 2-chlorocyclohexanone (215 mg 1.6 mmol) in anhydrous EtOH (8 mL) was stirred at 70° C. for 48 h. The reaction was cooled, and the solvent was removed under reduced pressure. The residue was purified by silica gel flash chromatography (2:1 hexanes/ethyl acetate) to provide the title compound (62 mg, 58%) as clear oil. LC-MS: RT=4.08 min, (M+H)+ 522.5.

Workup

  1. temperatureThe reaction was cooled
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was purified by silica gel flash chromatography (2:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-376ffaab431d4998aede5f62acc3c778
Source dataset
uspto-grants-2010_05
Patent number
US07714004B2

Reaction notes

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