Water → HCID 68998112, compound

HRID 1821380Notes

Reaction equation

HRID 1821380 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[CH:11][C:12]2[CH:22]=[CH:21][CH:20]=[CH:19][C:13]=2/[C:14](/[NH:17]O)=[N:15]\[H])=[N:2]1.[C:23]([O:27][CH3:28])(=[O:26])[C:24]#[CH:25].O>CO>[CH3:28][O:27][C:23]([C:24]1[NH:15][C:14]([C:13]2[CH:19]=[CH:20][CH:21]=[CH:22][C:12]=2/[CH:11]=[CH:10]/[C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][N:2]=2)=[N:17][CH:25]=1)=[O:26]

Participants

5

Reactant 3

HCID 962WaterHCID 13536Methyl propiolateHCID 178506493HCID 178506493, compound

Product 1

HCID 68998112HCID 68998112, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(E)-2-[2-(1H-indazol-3-yl)vinyl]-N-hydroxybenzamidine (0.30 g, 0.83 mmol) obtained in Step 1 of Example 175 was dissolved in methanol (8.0 mL) and after heating methyl propiolate (0.21 mL, 2.5 mmol) under reflux for 5 hours, water was added to stop the reaction. The mixture was extracted with ethyl acetate and the organic layer was concentrated. The residue was purified by preparative thin-layer chromatography (chloroform/acetone=4/1) to obtain Compound 195 (13 mg, 5%).

Workup

  1. temperatureunder reflux for 5 hours
  2. customthe reaction
  3. extractionThe mixture was extracted with ethyl acetate
  4. concentrationthe organic layer was concentrated
  5. customThe residue was purified by preparative thin-layer chromatography (chloroform/acetone=4/1)

Sources & evidence

ORD record
ord-ac50f330ac754ab99ac655c1397ceaa9
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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