5-Isocyanatoisoquinoline → N-(4-bromo-3-fluorobenzyl)-N'-(3-methyl-5-isoquinolinyl)urea

HRID 585980Notes

Reaction equation

[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][C:3]=1[F:10].[N:11]([C:14]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:15]=1[CH:16]=[C:17]([CH3:24])[N:18]=[CH:19]2)=[C:12]=[O:13].N(C1C=CC=C2C=1C=CN=C2)=C=O>>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][C:12]([NH:11][C:14]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:15]=2[CH:16]=[C:17]([CH3:24])[N:18]=[CH:19]3)=[O:13])=[CH:4][C:3]=1[F:10]

Participants

Reactant 3

HCID 115863575-Isocyanatoisoquinoline

HCID 222283825-Isocyanato-3-methylisoquinoline

HCID 22337664(4-Bromo-3-fluorophenyl)methanamine

Product 1

HCID 10430331N-(4-bromo-3-fluorobenzyl)-N'-(3-methyl-5-isoquinolinyl)urea

Procedure

The title compound was prepared using the procedure described in Example 61B using 4-bromo-3-fluorobenzylamine and the product from Example 154A instead of 4-cyanobenzyl alcohol and the product from Example 61A. 1H NMR (300 MHz, DMSO-d6) δ 9.68 (s, 1H), 9.46 (s, 1H), 8.51 (m, 2H), 8.01 (d, 1H, J=7.8 Hz), 7.80 (t, 1H, J=7.8 Hz), 7.67 (m, 2H), 7.36 (dd, 1H, J=9, 1.5 Hz), 7.18 (dd, 1H, J=9, 1 Hz), 4.39 (d, 2H, J=6 Hz), 2.77 (s, 3H); MS (ESI) 388/390 (M+H)+; Anal. Calcd for C18H15BrFN3O.HCl: C, 50.91; H, 3.80; N, 9.89. Found: C, 50.81; H, 3.74; N, 9.87

Sources & evidence

ORD record: ord-4dd94e53f42248678a45ae7b73ff51d7
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06933311B2

Reaction notes

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