Acetic Acid → HCID 178518357, compound

HRID 2236805Notes

Reaction equation

HRID 2236805 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+].[O:42]1[CH:46]=[CH:45][C:44]([CH:47]=O)=[CH:43]1.C(O)(=O)C.C(=O)(O)[O-].[Na+]>CN1CCCC1=O.C(Cl)Cl>[O:42]1[CH:46]=[CH:45][C:44]([CH2:47][N:25]2[CH2:24][CH2:23][N:22]([C:19]3[CH:18]=[CH:17][C:16]([NH:15]/[CH:14]=[C:5]4\[C:6](=[O:13])[NH:7][C:8](=[O:12])[C:9]5[C:4]\4=[CH:3][C:2]([I:1])=[CH:11][CH:10]=5)=[CH:21][CH:20]=3)[CH2:27][CH2:26]2)=[CH:43]1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 103513-FuraldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 178518347HCID 178518347, compound

Product 1

HCID 178518357HCID 178518357, compoundYield 81.2%

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 (47.4 mg, 0.1 mmol) is dissolved in N-methylpyrrolidinone (1 mL) and methylene chloride (0.3 mL), followed by addition of sodium triacetoxyborohydride (244 mg, 1.15 mmol), furan-3-carbaldehyde (0.214 mL, 2.58 mmol) and acetic acid (0.15 mL, 2.6 mmol). After stirring at room temperature for 40 min, methylene chloride and saturated sodium bicarbonate solution were added. The organic layer is separated and dried to give 45 mg (81%) of the title compound as an orange solid. MS (ESI) m/z 555.4 (M+H)+1.

Workup

  1. customThe organic layer is separated
  2. customdried

Sources & evidence

ORD record
ord-c4b2355122324ec7b7e677183ce6583c
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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