Isovaleryl chloride → HCID 178447226, compound

HRID 2236918Notes

Reaction equation

HRID 2236918 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][NH:7][CH:8]=[C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[O:19])[NH:11][C:10]2=[O:20])=[CH:4][CH:3]=1.[C:23](Cl)(=[O:28])[CH2:24][CH:25]([CH3:27])[CH3:26]>N1C=CC=CC=1.CN(C)C=O>[O:19]=[C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9](=[CH:8][NH:7][CH2:6][C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:23](=[O:28])[CH2:24][CH:25]([CH3:27])[CH3:26])=[CH:22][CH:21]=2)[C:10](=[O:20])[NH:11]1

Participants

5

Reactant 2

HCID 66054Isovaleryl chlorideHCID 178507621HCID 178507621, compound

Product 1

HCID 178447226HCID 178447226, compoundYield 98.6%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4-[(4-Amino-benzylamino)-methylene]-4H-isoquinoline-1,3-dione (29.3 mg, 0.1 mmol) in pyridine (250 μL) is added isovaleryl chloride (26 μL, 0.2 mmol). The reaction mixture is shaken at room temperature for 1 hour. The reaction mixture is diluted to 2 mL with N,N-dimethylformamide and purified by C18 reverse phase HPLC. The pure fractions were combined and concentrated to yield the title compound (37.2 mg).

Workup

  1. custompurified by C18 reverse phase HPLC
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-86cd693ce9d147769f251c9334bdbcb5
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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