Dichloroacetyl chloride → HCID 178518270, compound

HRID 2236768Notes

Reaction equation

HRID 2236768 reaction equation
OC1C=C(CN/C=C2\C(=O)NC(=O)C3C\2=CC(I)=CC=3)C=CC=1NC(=O)C1C=CC=CC=1.[NH2:33][C:34]1[CH:55]=[CH:54][C:37]([CH2:38][NH:39]/[CH:40]=[C:41]2\[C:42](=[O:53])[NH:43][C:44](=[O:52])[C:45]3[C:50]\2=[CH:49][C:48]([Br:51])=[CH:47][CH:46]=3)=[CH:36][C:35]=1[O:56][Si](C(C)C)(C(C)C)C(C)C.[Cl:67][CH:68]([Cl:72])[C:69](Cl)=[O:70]>>[Br:51][C:48]1[CH:49]=[C:50]2[C:45](=[CH:46][CH:47]=1)[C:44](=[O:52])[NH:43][C:42](=[O:53])/[C:41]/2=[CH:40]\[NH:39][CH2:38][C:37]1[CH:54]=[CH:55][C:34]([NH:33][C:69](=[O:70])[CH:68]([Cl:72])[Cl:67])=[C:35]([OH:56])[CH:36]=1

Participants

4

Reactant 3

HCID 6593Dichloroacetyl chlorideHCID 178460971HCID 178460971, compoundHCID 178518369N-[2-hydroxy-4-[[[(Z)-(6-iodo-1,3-dioxoisoquinolin-4-ylidene)methyl]amino]methyl]phenyl]benzamide

Product 1

HCID 178518270HCID 178518270, 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 (60 mg, 0.11 mmol) is reacted with dichloroacetyl chloride (110 μL, 1.1 mmol). Following desilylation and precipitation, N-[4-({[(Z)-(6-bromo-1,3-dioxo-2,3-dihydroisoquinolin-4(1H)-ylidene)methyl]amino}methyl)-2-hydroxyphenyl]-2,2-dichloroacetamide is obtained 8.8 mg, 16%).

Workup

  1. customdesilylation and precipitation

Sources & evidence

ORD record
ord-1529b1c371904150be060068bae56532
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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