Citric Acid → HCID 59135672, compound

HRID 1960317Notes

Reaction equation

HRID 1960317 reaction equation
C([O:3][C:4](=[O:36])[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[NH:27][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.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.[Cl-].[Na+]>O1CCCC1.C(OCC)(=O)C.CO>[S:32]1[CH:33]=[CH:34][CH:35]=[C:31]1[S:28]([NH:27][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[CH2:10][CH2:11][N:6]([CH2:5][C:4]([OH:36])=[O:3])[CH2:7][CH2:8]3)=[CH:14][N:15]=1)=[CH:26]2)(=[O:29])=[O:30]

Participants

8

Reactant 4

HCID 311Citric AcidHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 59136017ethyl {4-[(2-{7-[(2-thienylsulfonyl)amino]-1H-indol-2-yl}-1,3-thiazol-5-yl)methyl]piperazin-1-yl}acetate

Product 1

HCID 59135672HCID 59135672, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl{4-[(2-{7-[(2-thienylsulfonyl)amino]-1H-indol-2-yl}-1,3-thiazol-5-yl)methyl]piperazin-1-yl}acetate (0.500 g) in a mixed solvent of tetrahydrofuran (15 ml) and methanol (5 ml) was added 2N aqueous sodium hydroxide solution (1.5 ml), and the mixture was stirred at 50° C. for 2 hr. 10% Aqueous citric acid solution, ethyl acetate, sodium chloride and tetrahydrofuran were successively added to the reaction solution, and the precipitated crystals were collected by filtration, washed with ethyl acetate, and dried to give the title compound (0.360 g, yield 76%) as colorless crystals.

Workup

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

Sources & evidence

ORD record
ord-be3bb0865fd24c32b5488e8599f76ffd
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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