Propionyl chloride → N-[2-hydroxy-4-[[[(Z)-(6-iodo-1,3-dioxoisoquinolin-4-ylidene)methyl]amino]methyl]phenyl]-2-methylpropanamide

HRID 2236780Notes

Reaction equation

HRID 2236780 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH2:8][NH:9]/[CH:10]=[C:11]2\[C:12](=[O:23])[NH:13][C:14](=[O:22])[C:15]3[C:20]\2=[CH:19][C:18]([I:21])=[CH:17][CH:16]=3)[CH:5]=[CH:4][C:3]=1[NH:24][C:25](=[O:32])[C:26]1[CH:31]=CC=C[CH:27]=1.NC1C=CC(CN/C=C2\C(=O)NC(=O)C3C\2=CC(I)=CC=3)=CC=1O[Si](C(C)C)(C(C)C)C(C)C.C(Cl)(=O)CC>>[OH:1][C:2]1[CH:7]=[C:6]([CH2:8][NH:9]/[CH:10]=[C:11]2\[C:12](=[O:23])[NH:13][C:14](=[O:22])[C:15]3[C:20]\2=[CH:19][C:18]([I:21])=[CH:17][CH:16]=3)[CH:5]=[CH:4][C:3]=1[NH:24][C:25](=[O:32])[CH:26]([CH3:27])[CH3:31]

Participants

4

Reactant 3

HCID 62324Propionyl chlorideHCID 178460972HCID 178460972, compoundHCID 178518369N-[2-hydroxy-4-[[[(Z)-(6-iodo-1,3-dioxoisoquinolin-4-ylidene)methyl]amino]methyl]phenyl]benzamide

Product 1

HCID 178454464N-[2-hydroxy-4-[[[(Z)-(6-iodo-1,3-dioxoisoquinolin-4-ylidene)methyl]amino]methyl]phenyl]-2-methylpropanamide

Procedure

Following the acetylation and desilylation procedure employed for the preparation of N-[2-hydroxy-4-({[(Z)-(6-iodo-1,3-dioxo-2,3-dihydroisoquinolin-4(1H)-ylidene)methyl]amino}methyl)phenyl]benzamide, (4Z)-4-[({4-amino-3-[(triisopropylsilyl)oxy]benzyl}amino)methylene]-6-iodoisoquinoline-1,3(2H,4H)-dione (75 mg, 0.13 mmol) is reacted with propionyl chloride (110 μL, 1.3 mmol). Following desilylation and precipitation, N-[2-hydroxy-4-({[(Z)-(6-iodo-1,3-dioxo-2,3-dihydroisoquinolin-4(1H)-ylidene)methyl]amino}methyl)phenyl]-2-methylpropanamide is obtained (9.3 mg, 15%).

Workup

  1. customdesilylation and precipitation

Sources & evidence

ORD record
ord-f194cc8ae3374de0b5ab49d3937ce42d
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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