Acetaldehyde → HCID 68999737, compound

HRID 1821381Notes

Reaction equation

HRID 1821381 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1/[CH:18]=[CH:19]/[C:20]1[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:22][N:21]=1)[C:5]2=[O:29].[CH:30](=O)[CH3:31].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C1COCC1>[CH2:30]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1/[CH:18]=[CH:19]/[C:20]1[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:22][N:21]=1)[C:5]2=[O:29])[CH3:31]

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 11509161HCID 11509161, compound

Product 1

HCID 68999737HCID 68999737, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (E)-5-amino-2-{2-[2-(1H-indazol-3-yl)vinyl]phenyl}isoindole-1,3-dione (40 mg, 0.11 mmol) obtained in Example 193 in THF (1.0 mL), acetaldehyde (5.2 μL, 0.12 mmol) and sodium triacetoxyborohydride (33 mg, 0.16 mmol) were added and stirred at room temperature for 2.5 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate solution, extracted with ethyl acetate and the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform to chloroform/methanol=90/10) to obtain Compound 201 (16 mg, 38%).

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationthe organic layer was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (chloroform to chloroform/methanol=90/10)

Sources & evidence

ORD record
ord-01ea333f9b354e2da524af31ed556591
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

Loading…