Acryloyl chloride → HCID 178460028, compound

HRID 2236752Notes

Reaction equation

HRID 2236752 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)=[CH:17][CH:16]=3)[CH:5]=[CH:4][C:3]=1[NH:24][C:25](=[O:32])[C:26]1C=CC=C[CH:27]=1.NC1C=CC(CN/C=C2\C(=O)NC(=O)C3C\2=CC([Br:51])=CC=3)=CC=1O[Si](C(C)C)(C(C)C)C(C)C.C(Cl)(=O)C=C>>[Br:51][C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[C:14](=[O:22])[NH:13][C:12](=[O:23])/[C:11]/2=[CH:10]\[NH:9][CH2:8][C:6]1[CH:5]=[CH:4][C:3]([NH:24][C:25](=[O:32])[CH:26]=[CH2:27])=[C:2]([OH:1])[CH:7]=1

Participants

4

Reactant 3

HCID 13140Acryloyl chlorideHCID 178460971HCID 178460971, compoundHCID 178518369N-[2-hydroxy-4-[[[(Z)-(6-iodo-1,3-dioxoisoquinolin-4-ylidene)methyl]amino]methyl]phenyl]benzamide

Product 1

HCID 178460028HCID 178460028, compound

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-bromoisoquinoline-1,3(2H,4H)-dione (54 mg, 0.10 mmol) is reacted with acryloyl chloride (41 μL, 0.50 mmol). Following desilylation, precipitation, and washing with methanol and diethyl ether, N-[4-({[(Z)-(6-bromo-1,3-dioxo-2,3-dihydroisoquinolin-4(1H)-ylidene)methyl]amino}methyl)-2-hydroxyphenyl]acrylamide is obtained (8 mg, 18

Workup

  1. customdesilylation, precipitation
  2. washwashing with methanol and diethyl ether

Sources & evidence

ORD record
ord-d42724c20c8f4ff99a0abc2c5998d37f
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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