Acetohydrazide → HCID 66581078, compound

HRID 1521824Notes

Reaction equation

HRID 1521824 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]2[CH2:27][S:26](=[O:29])(=[O:28])[C:25]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:8]=2[N:9]([C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=2)[C:14]([OH:16])=O)[N:10]=1)=[O:5])[CH3:2].[C:30]([NH:33][NH2:34])(=O)[CH3:31]>CCOC(C)=O>[CH3:31][C:30]1[O:16][C:14]([C:13]2[CH:12]=[C:11]([N:9]3[C:8]4[C:20]5[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=5[S:26](=[O:29])(=[O:28])[CH2:27][C:7]=4[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[N:10]3)[CH:19]=[CH:18][CH:17]=2)=[N:34][N:33]=1

Participants

4

Reactant 2

HCID 14039AcetohydrazideHCID 66579076HCID 66579076, compound

Product 1

HCID 66581078HCID 66581078, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-[3-(ethoxycarbonyl)-5,5-dioxidothiochromeno[4,3-c]pyrazol-1(4H)-yl]benzoic acid (200 mg, 0.485 mmol) in EtOAc is added acetic hydrazide (35 mg, 0.485 mmol) under nitrogen. Then TEA (0.2 mL, 1.45 mmol) and propane phosphonic acid cyclic anhydride (0.7 mL, 1.2 mmol) is added to the reaction mixture at 0° C. under nitrogen. The reaction mixture is refluxed at 80° C. for 12 h after which it is diluted with EtOAC and washed with 10% aq. Na2CO3 solution. The organic layer is separated, dried over Na2SO4 and concentrated under reduced pressure. The solid residue is purified by silica gel column chromatography over (1.5% MeOH in DCM to afford the title compound. MS (ESI+): 451.2.

Workup

  1. additionis diluted with EtOAC
  2. washwashed with 10% aq. Na2CO3 solution
  3. customThe organic layer is separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe solid residue is purified by silica gel column chromatography over (1.5% MeOH in DCM

Sources & evidence

ORD record
ord-d05b0fcd4e1447c597944d8324a5412f
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

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