Citric Acid → HCID 136060820, compound

HRID 1851539Notes

Reaction equation

HRID 1851539 reaction equation
[H-].[Na+].[C:3]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl[CH2:15][C:16]1[N:17]=[C:18]([C:21]2[NH:22][C:23]3[C:28]([CH:29]=2)=[CH:27][CH:26]=[CH:25][C:24]=3[N:30]([CH3:39])[S:31]([C:34]2[S:35][CH:36]=[CH:37][CH:38]=2)(=[O:33])=[O:32])[S:19][CH:20]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[CH3:39][N:30]([S:31]([C:34]1[S:35][CH:36]=[CH:37][CH:38]=1)(=[O:33])=[O:32])[C:24]1[CH:25]=[CH:26][CH:27]=[C:28]2[C:23]=1[NH:22][C:21]([C:18]1[S:19][CH:20]=[C:16]([CH2:15][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:3]([O:11][CH2:12][CH3:13])=[O:10])[N:17]=1)=[CH:29]2

Participants

6

Reactant 4

HCID 311Citric AcidHCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 136060814HCID 136060814, compound

Product 1

HCID 136060820HCID 136060820, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60% in oil, 0.15 g) in N,N-dimethylformamide (10 mL) was added diethyl malonate (0.53 g) at 0° C., and the mixture was stirred for 30 min. To the reaction mixture was added N-{2-[4-(chloromethyl)-1,3-thiazol-2-yl]-1H-indol-7-yl}-N-methylthiophene-2-sulfonamide (0.45 g) at 0° C., and the mixture was stirred at room temperature for 3 hr. To the reaction mixture was added 10% citric acid was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was subjected to silica gel column chromatography and the title compound (0.43 g, yield 72%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (2:3, volume ratio).

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hr
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-57aa384f4b304e559d89c78c8d4c00b5
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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