5-Aminoisoquinoline → N-5-isoquinolinyl-N'-pentylurea

HRID 2056848Notes

Reaction equation

[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[C:2]=[O:3].[CH:9]1[C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([NH2:19])[C:13]=2[CH:12]=[CH:11][N:10]=1.BrC1C=CC(CN=C=O)=CC=1>>[CH:9]1[C:18]2[C:13](=[C:14]([NH:19][C:2]([NH:1][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[O:3])[CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][N:10]=1

Participants

Reactant 3

HCID 707665-Aminoisoquinoline

HCID 206036Pentane, 1-isocyanato-

HCID 43746174-Bromobenzyl isocyanate

Product 1

HCID 22032627N-5-isoquinolinyl-N'-pentylurea

Procedure

The title compound was prepared using the procedure described in Example 60F using 1-isocyanatopentane and 5-isoquinolinamine instead of the product from Example 60E and 1-bromo-4-(isocyanatomethyl)benzene. NMR (DMSO-d6) δ 9.70 (s, 1H), 9.19 (s, 1H), 8.64 (d, 1H), 8.57 (m, 2H), 8.01 (d, 1H), 7.84 (d, 1H), 7.85 (t, 1H), 6.95 (m, 1H), 3.17 (m, 2H), 2.48 (m, 2H), 1.23 (m, 4H), 0.86 (M, 3H); MS (ESI) (M+H)+339.

Sources & evidence

ORD record: ord-555ecc788c10405b88dc52653fe9c3d3
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07335678B2

Reaction notes

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