Potassium Carbonate → 7-Oxo-5-phenyl-N-{3-[4-[2-(2,2,2-trifluoroethoxy)phenyl]-1-piperazinyl]propyl}-7H-thieno[3,2-b]pyran-3-carboxamide

HRID 381287Notes

Reaction equation

HRID 381287 reaction equation
Cl[CH2:2][CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:12]2[O:13][C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:15][C:16](=[O:17])[C:11]=2[S:10][CH:9]=1)=[O:7].[F:24][C:25]([F:41])([F:40])[CH2:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1.C(=O)([O-])[O-].[K+].[K+]>>[O:17]=[C:16]1[CH:15]=[C:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:13][C:12]2[C:8]([C:6]([NH:5][CH2:4][CH2:3][CH2:2][N:37]3[CH2:36][CH2:35][N:34]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=4[O:27][CH2:26][C:25]([F:40])([F:24])[F:41])[CH2:39][CH2:38]3)=[O:7])=[CH:9][S:10][C:11]1=2

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 104915651-[2-(2,2,2-Trifluoroethoxy)phenyl]piperazineHCID 22464456N-(3-Chloropropyl)-7-oxo-5-phenyl-7H-thieno[3,2-b]pyran-3-carboxamide

Product 1

HCID 99379847-Oxo-5-phenyl-N-{3-[4-[2-(2,2,2-trifluoroethoxy)phenyl]-1-piperazinyl]propyl}-7H-thieno[3,2-b]pyran-3-carboxamideYield 70%

Conditions

Temperature
200 °C

Procedure

A mixture of 0.17 g of Compound 5A, 0.13 g of 1-[2-(2,2,2-trifluoroethoxy)phenyl]-piperazine (prepared as described by EP 0748 800, G. Bantle et al.) and 0.07 g of potassium carbonate was heated at 200° C. for 20 minutes. After cooling to 20-25° C., the crude residue was purified by flash chromatography in ethyl acetate/methanol gradient (95:5 to 9:1) to yield 0.193 g (70%) of the title compound. M.p. 152-158° C.

Workup

  1. temperatureAfter cooling to 20-25° C.
  2. customthe crude residue was purified by flash chromatography in ethyl acetate/methanol gradient (95:5 to 9:1)

Sources & evidence

ORD record
ord-98f8e943100e4ab9a3087b38e421c7be
Source dataset
uspto-grants-2001_10
Patent number
US06306861B1

Reaction notes

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