Tetrahydrofuran → {4-[(2-{7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl)-1,3-thiazol-5-yl)methyl]piperazin-1-yl}acetic acid

HRID 1960313Notes

Reaction equation

HRID 1960313 reaction equation
C([O:3][C:4](=[O:37])[CH2:5][N:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[S:17][C:16]([C:18]3[NH:19][C:20]4[C:25]([CH:26]=3)=[CH:24][CH:23]=[CH:22][C:21]=4[N:27]([CH3:36])[S:28]([C:31]3[S:32][CH:33]=[CH:34][CH:35]=3)(=[O:30])=[O:29])=[N:15][CH:14]=2)[CH2:8][CH2:7]1)C.O1CCCC1.[OH-].[Na+].[Cl-].[NH4+]>CO>[CH3:36][N:27]([S:28]([C:31]1[S:32][CH:33]=[CH:34][CH:35]=1)(=[O:30])=[O:29])[C:21]1[CH:22]=[CH:23][CH:24]=[C:25]2[C:20]=1[NH:19][C:18]([C:16]1[S:17][C:13]([CH2:12][N:9]3[CH2:8][CH2:7][N:6]([CH2:5][C:4]([OH:37])=[O:3])[CH2:11][CH2:10]3)=[CH:14][N:15]=1)=[CH:26]2

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 59303517ethyl{4-[(2-{7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-1,3-thiazol-5-yl)methyl]piperazin-1-yl)acetate

Product 1

HCID 59135617{4-[(2-{7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl)-1,3-thiazol-5-yl)methyl]piperazin-1-yl}acetic acidYield 77.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl{4-[(2-{7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-1,3-thiazol-5-yl)methyl]piperazin-1-yl}acetate (0.490 g) in a mixed solvent of tetrahydrofuran (10 ml) and methanol (5 ml) was added 8N aqueous sodium hydroxide solution (1.5 ml), and the mixture was stirred at room temperature for 16 hr. Saturated aqueous ammonium chloride solution was added to the reaction solution, and the precipitated crystals were collected by filtration, washed with ethyl acetate and water, and dried to give the title compound (0.360 g, yield 57%) as colorless crystals.

Workup

  1. filtrationthe precipitated crystals were collected by filtration
  2. washwashed with ethyl acetate and water
  3. customdried

Sources & evidence

ORD record
ord-f0a465d1768e4ee792c474b3fa28b3f8
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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