Acetic Acid → HCID 178456342, compound

HRID 2236801Notes

Reaction equation

HRID 2236801 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/2=[CH:14]\[NH:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[CH:18][CH:17]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:42][C:43]([CH3:45])=O.C(O)(=O)C.C(=O)(O)[O-].[Na+]>CN1CCCC1=O.C(Cl)Cl>[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/2=[CH:14]\[NH:15][C:16]1[CH:17]=[CH:18][C:19]([N:22]2[CH2:23][CH2:24][N:25]([CH:43]([CH3:45])[CH3:42])[CH2:26][CH2:27]2)=[CH:20][CH:21]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 180AcetoneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 178518347HCID 178518347, compound

Product 1

HCID 178456342HCID 178456342, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

(4Z)-6-iodo-4-{[(4-piperazin-1-ylphenyl)amino]methylene}isoquinoline-1,3(2H,4H)-dione (23.7 mg, 0.05 mmol) is dissolved in N-methylpyrrolidinone (0.5 mL) and methylene chloride (0.15 mL), followed by addition of sodium triacetoxyborohydride (122 mg, 0.575 mmol), acetone (0.095 mL, 1.29 mmol) and acetic acid (0.075 mL, 1.31 mmol). After stirring at room temperature for 1 h, methylene chloride and saturated sodium bicarbonate solution were added. The organic layer is separated and dried to give 18.8 mg (73%) of the title compound as a yellow solid. MS (ESI) m/z 517.0 (M+H)+1

Workup

  1. customThe organic layer is separated
  2. customdried

Sources & evidence

ORD record
ord-8ffbfe57587c4472bde5c539e3ea6c0e
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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