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

HRID 585990Notes

Reaction equation

HRID 585990 reaction equation
[N:1]1([C:9]2[CH:16]=[CH:15][C:12]([CH2:13][NH2:14])=[CH:11][C:10]=2[F:17])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N:18]([C:21]1[CH:30]=[CH:29][CH:28]=[C:27]2[C:22]=1[CH:23]=[C:24]([CH3:31])[N:25]=[CH:26]2)=[C:19]=[O:20].N(C1C=CC=C2C=1C=CN=C2)=C=O>>[N:1]1([C:9]2[CH:16]=[CH:15][C:12]([CH2:13][NH:14][C:19]([NH:18][C:21]3[CH:30]=[CH:29][CH:28]=[C:27]4[C:22]=3[CH:23]=[C:24]([CH3:31])[N:25]=[CH:26]4)=[O:20])=[CH:11][C:10]=2[F:17])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 115863575-IsocyanatoisoquinolineHCID 222283825-Isocyanato-3-methylisoquinolineHCID 223375744-(1-Azocanyl)-3-fluorobenzylamine

Product 1

HCID 22032674N-[4-(1-azocanyl)-3-fluorobenzyl]-N'-(3-methyl-5-isoquinolinyl)urea

Procedure

The title compound was prepared using the procedure described in Example 61B using 4-(1-azocanyl)-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 9.70 (s, 1H), 9.37 (s, 1H), 8.56 (m, 2H), 8.01 (d, 1H, J=8.4 Hz), 7.81 (t, 1H, J=8.4 Hz), 7.45 (t, 1H), 7.02 (m, 2H), 6.90 (m, 1H), 4.25 (d, 2H, J=6 Hz), 3.35 (m, 4H), 2.77 (s, 3H), 1.67 (m, 4H), 1.54 (m, 6H); MS (ESI) 421 (M+H)+; Anal. Calcd for C25H29FN4O.HCl: C, 65.71; H, 6.62; N, 12.26. Found: C, 65.44; H, 6.49; N, 12.15.

Sources & evidence

ORD record
ord-de8bcf7c92be426f997d95ae11c1dfa0
Source dataset
uspto-grants-2005_08
Patent number
US06933311B2

Reaction notes

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