5-Isocyanatoisoquinoline → N-[4-(1-azepanyl)benzyl]-N'-(3-methyl-5-isoquinolinyl)urea

HRID 585985Notes

Reaction equation

HRID 585985 reaction equation
[N:1]1([C:8]2[CH:15]=[CH:14][C:11]([CH2:12][NH2:13])=[CH:10][CH:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N:16]([C:19]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:20]=1[CH:21]=[C:22]([CH3:29])[N:23]=[CH:24]2)=[C:17]=[O:18].N(C1C=CC=C2C=1C=CN=C2)=C=O>>[N:1]1([C:8]2[CH:9]=[CH:10][C:11]([CH2:12][NH:13][C:17]([NH:16][C:19]3[CH:28]=[CH:27][CH:26]=[C:25]4[C:20]=3[CH:21]=[C:22]([CH3:29])[N:23]=[CH:24]4)=[O:18])=[CH:14][CH:15]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 115863575-IsocyanatoisoquinolineHCID 222283825-Isocyanato-3-methylisoquinolineHCID 22337561[4-(Azepan-1-YL)phenyl]methanamine

Product 1

HCID 9977590N-[4-(1-azepanyl)benzyl]-N'-(3-methyl-5-isoquinolinyl)urea

Procedure

The title compound was prepared using the procedure described in Example 61B using 4-(1-azepanyl)benzylamine and the product from Example 154A instead of 4-cyanobenzyl alcohol and the product from Example 61A. 1H NMR (300 MHz, DMSO-d6) δ 9.16 (s, 1H), 8.53 (s, 1H), 8.28 (d, 1H, J=8 Hz), 7.74 (s, 1H), 7.67 (d, 1H, J=8 Hz), 7.50 (t, 1H, J=8 Hz), 7.14 (d, 2H, J=9 Hz), 6.84 (t, 1H, J=6 Hz), 6.66 (d, 2H, J=9 Hz), 4.20 (d, 2H, J=6 Hz), 3.44 (m, 4H), 2.63 (s, 3H), 1.71 (m, 4H), 1.45 (m, 4H). MS (ESI) 389 (M+H)+; Anal. Calcd for C24H28N4O.0.3H2O: C, 73.18; H, 7.32; N, 14.22. Found: C, 73.08; H, 7.38; N, 14.22.

Sources & evidence

ORD record
ord-14830f1b83ee42d2bd35e70972db6c37
Source dataset
uspto-grants-2005_08
Patent number
US06933311B2

Reaction notes

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