Benzenemethanamine, 3,4-dichloro- → N-(3,4-dichlorobenzyl)-N'-(3-methylcinnolin-5-yl)urea

HRID 585909Notes

Reaction equation

HRID 585909 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH2:5][NH2:6].ClC(Cl)(Cl)[C:13]([NH:15][C:16]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:17]=1[CH:18]=[C:19]([CH3:26])[N:20]=[N:21]2)=[O:14].C1CCN2C(=NCCC2)CC1>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH2:5][NH:6][C:13]([NH:15][C:16]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:17]=1[CH:18]=[C:19]([CH3:26])[N:20]=[N:21]2)=[O:14]

Participants

4

Reactant 3

HCID 1608Benzenemethanamine, 3,4-dichloro-HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 220326582,2,2-trichloro-N-(3-methylcinnolin-5-yl)acetamide

Product 1

HCID 10406258N-(3,4-dichlorobenzyl)-N'-(3-methylcinnolin-5-yl)urea

Procedure

The title compound was prepared using 3,4-dichlorobenzylamine, the product from Example 16A, DBU and the procedure described in Example 1B. MS (ESI+) m/z 362 (M+H)+; 1H NMR (DMSO-d6) δ 2.88 (s, 3H), 4.36 (d, 2H), 7.10 (t, 1H), 7.34 (dd, 1H), 7.59 (m, 2H), 7.76 (t, 1H), 8.04 (d, 2H), 8.19 (d, 1H), 8.93 (s, 1H).

Sources & evidence

ORD record
ord-e490038f1d0e4965a81eed8c296aaaa7
Source dataset
uspto-grants-2005_08
Patent number
US06933311B2

Reaction notes

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