1,2-Dichloro-4-(isocyanatomethyl)benzene → HCID 11364907, compound

HRID 2354698Notes

Reaction equation

HRID 2354698 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[Cl:12])[CH2:5][N:6]=[C:7]=[O:8].[NH2:13][C:14]1[N:19]=[N:18][C:17]([N:20]2[CH2:25][CH2:24][N:23]([C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]([F:37])([F:36])[F:35])=[O:27])[CH2:22][CH2:21]2)=[CH:16][CH:15]=1>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[Cl:12])[CH2:5][NH:6][C:7]([NH:13][C:14]1[N:19]=[N:18][C:17]([N:20]2[CH2:21][CH2:22][N:23]([C:26](=[O:27])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]([F:37])([F:36])[F:35])[CH2:24][CH2:25]2)=[CH:16][CH:15]=1)=[O:8]

Participants

3

Reactant 2

HCID 27333681,2-Dichloro-4-(isocyanatomethyl)benzeneHCID 66849536[4-(6-Aminopyridazin-3-yl)piperazin-1-yl](2-trifluoromethylphenyl)methanone

Product 1

HCID 11364907HCID 11364907, compound

Procedure

Following the procedure of Example 5, making variations only as required to use 3,4-dichlorobenzylisocyanate in place of (2-isocyanato-cyclopropyl)benzene to react with [4-(6-aminopyridazin-3-yl)piperazin-1-yl](2-trifluoromethylphenyl)-methanone, the title compound was obtained as white powder (44% yield). 1H NMR (300 MHz, DMSO-d6) δ 9.38, 8.30, 7.85, 7.77, 7.67, 7.59, 7.52-7.57, 7.39, 7.29, 4.38, 3.70-3.82, 3.50-3.62, 3.42-3.47, 3.34-3.38, 3.23-3.29, 3.15-3.20. MS (ES+) m/z 553 (M+1).

Sources & evidence

ORD record
ord-35707b532ff84ecd98e0a995eee89bf3
Source dataset
uspto-grants-2010_07
Patent number
US07754711B2

Reaction notes

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