Isopropanol → ethyl((1S)-5-{3-[4-(4-isopropoxy-1,3-thiazol-2-yl)-2-methoxyphenoxy]propoxy}-2,3-dihydro-1h-inden-1-yl)acetate

HRID 603426Notes

Reaction equation

HRID 603426 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[CH2:33][C:34](N(C)C)=[O:35].[CH3:39][CH:40](O)[CH3:41]>>[CH2:26]([O:25][C:23](=[O:24])[CH2:22][C@H:18]1[C:19]2[C:15](=[CH:14][C:13]([O:12][CH2:11][CH2:10][CH2:9][O:8][C:7]3[CH:28]=[CH:29][C:4]([C:2]4[S:3][CH:33]=[C:34]([O:35][CH:40]([CH3:41])[CH3:39])[N:1]=4)=[CH:5][C:6]=3[O:30][CH3:31])=[CH:21][CH:20]=2)[CH2:16][CH2:17]1)[CH3:27]

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 758862-chloro-N,N-dimethylacetamideHCID 16110447ethyl ((1S)-5-{3-[4-(aminocarbonothioyl)-2-methoxyphenoxy]propoxy)-2,3-dihydro-1H-inden-1-yl)acetate

Product 1

HCID 16110530ethyl((1S)-5-{3-[4-(4-isopropoxy-1,3-thiazol-2-yl)-2-methoxyphenoxy]propoxy}-2,3-dihydro-1h-inden-1-yl)acetateYield 49%

Procedure

A solution of ethyl ((1S)-5-{3-[4-(aminocarbonothioyl)-2-methoxyphenoxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate (500 mg, 1.1 mmol) (Example 146) and 2-chloro-N,N-dimethylacetamide (800 mg, 6.6 mmol) in i-PrOH (anhydrous, 15 mL) was stirred at 70° C. for 8 h. The reaction was cooled to rt, and concentrated under reduced pressure. Purification by silica gel flash chromatography (EtOAc:hexane (v/v)=1:2) gave 292 mg (49%) of the title compound as a yellow oil. LC-MS: RT=4.27 min; (M+H)+:526.1.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customPurification by silica gel flash chromatography (EtOAc:hexane (v/v)=1:2)

Sources & evidence

ORD record
ord-6ca5c1769fba423588cc31ab6f401c8f
Source dataset
uspto-grants-2011_03
Patent number
US07906653B2

Reaction notes

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