Crotonic anhydride → [2-[[(E)-but-2-enoyl]amino]-5-[[[(Z)-(6-iodo-1,3-dioxoisoquinolin-4-ylidene)methyl]amino]methyl]phenyl] (E)-but-2-enoate

HRID 2236784Notes

Reaction equation

HRID 2236784 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]1C=CC=C[CH:27]=1.NC1C=CC(CN/C=C2\C(=O)N[C:44](=[O:52])[C:45]3C\2=CC(I)=[CH:47][CH:46]=3)=CC=1O[Si](C(C)C)(C(C)C)C(C)C.[C:67](OC(=O)/C=C/C)(=O)/C=C/C>>[C:44]([O: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]=[CH:27]/[CH3:67])(=[O:52])/[CH:45]=[CH:46]/[CH3:47]

Participants

4

Reactant 3

HCID 6049834Crotonic anhydrideHCID 178460972HCID 178460972, compoundHCID 178518369N-[2-hydroxy-4-[[[(Z)-(6-iodo-1,3-dioxoisoquinolin-4-ylidene)methyl]amino]methyl]phenyl]benzamide

Product 1

HCID 178454465[2-[[(E)-but-2-enoyl]amino]-5-[[[(Z)-(6-iodo-1,3-dioxoisoquinolin-4-ylidene)methyl]amino]methyl]phenyl] (E)-but-2-enoate

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 (65 mg, 0.11 mmol) is reacted with crotonic anhydride (49 μL, 0.33 mmol). Following desilylation and precipitation, 2-[(2E)-but-2-enoylamino]-5-({[(Z)-(6-iodo-1,3-dioxo-2,3-dihydroisoquinolin-4(1H)-ylidene)methyl]amino}methyl)phenyl (2E)-but-2-enoate is obtained (17 mg, 27%)

Workup

  1. customdesilylation and precipitation

Sources & evidence

ORD record
ord-9e155bf3b7fd4db19f8a162d5d2abf03
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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