3-Fluorobenzyl isocyanate → N-(8-bromoisoquinolin-5-yl)-N'-(3-fluorobenzyl)urea

HRID 1791309Notes

Reaction equation

HRID 1791309 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][N:9]=[C:10]=[O:11])[CH:3]=1.[Br:12][C:13]1[C:22]2[CH:21]=[N:20][CH:19]=[CH:18][C:17]=2[C:16]([NH2:23])=[CH:15][CH:14]=1>>[Br:12][C:13]1[CH:14]=[CH:15][C:16]([NH:23][C:10]([NH:9][CH2:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)=[O:11])=[C:17]2[C:22]=1[CH:21]=[N:20][CH:19]=[CH:18]2

Participants

3

Reactant 2

HCID 6434993-Fluorobenzyl isocyanateHCID 220326308-Bromoisoquinolin-5-amine

Product 1

HCID 10248799N-(8-bromoisoquinolin-5-yl)-N'-(3-fluorobenzyl)urea

Procedure

The title compound was prepared using 1-fluoro-3-(isocyanatomethyl)benzene, the product of Example 73A and the procedure described in Example 73 (white solid, 108 mg, 65%). MS (ESI+) m/z 376 (M+H)+; MS (ESI−) m/z 374 (M−H)−; 1H NMR (DMSO-d6, 300 MHz) δ 4.39 (d, 5.8, 2H), 7.09 (m, 1H), 7.17 (m, 2H), 7.40 (m, 1H), 7.91 (d, J 8.5, 1H), 8.01 (d, J 6.1, 1H), 8.23 (d, J 8.5, 1H), 8.69 (d, J 5.8, 1H), 8.93 (s, 1H), 9.44 (s, 1H); Anal. Calcd for C17H13BrFN3O: C, 54.56; H, 3.50; N, 11.23. Found: C, 54.64; H, 3.33; N, 11.19.

Sources & evidence

ORD record
ord-fc1f90ba027d43989e6d6e60ee769702
Source dataset
uspto-grants-2006_07
Patent number
US07074805B2

Reaction notes

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