(4-Piperidinophenyl)methylamine → N-(3-methyl-5-isoquinolinyl)-N'-[4-(1-piperidinyl)benzyl]urea

HRID 887253Notes

Reaction equation

HRID 887253 reaction equation
[N:1]1([C:7]2[CH:14]=[CH:13][C:10]([CH2:11][NH2:12])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N:15]([C:18]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:19]=1[CH:20]=[C:21]([CH3:28])[N:22]=[CH:23]2)=[C:16]=[O:17].N(C1C=CC=C2C=1C=CN=C2)=C=O>>[CH3:28][C:21]1[N:22]=[CH:23][C:24]2[C:19]([CH:20]=1)=[C:18]([NH:15][C:16]([NH:12][CH2:11][C:10]1[CH:13]=[CH:14][C:7]([N:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)=[CH:8][CH:9]=1)=[O:17])[CH:27]=[CH:26][CH:25]=2

Participants

4

Reactant 3

HCID 2795551(4-Piperidinophenyl)methylamineHCID 115863575-IsocyanatoisoquinolineHCID 222283825-Isocyanato-3-methylisoquinoline

Product 1

HCID 9976700N-(3-methyl-5-isoquinolinyl)-N'-[4-(1-piperidinyl)benzyl]urea

Procedure

The title compound was prepared using the procedure described in Example 61B using 4-(1-piperidinyl)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 9.69 (s, 1H), 9.60 (s, 1H), 8.68 (s, 1H), 8.57 (d, 1H, J=7.5 Hz), 8.00 (d, 1H, J=7.5 Hz), 7.85-7.55 (m, 4H), 7.43 (m, 2H), 4.40 (d, 2H, J=6 Hz), 3.44 (m, 4H), 2.77 (s, 3H), 1.90 (m, 4H), 1.65 (m, 2H); MS (ESI) 375 (M+H)+; Anal. Calcd for C23H26N4O.2.4HCl: C, 59.80; H, 6.20; N, 12.13. Found: C, 59.91; H, 6.45; N, 11.78.

Sources & evidence

ORD record
ord-4dcec7a343fb4956926cce8c4b7171fd
Source dataset
uspto-grants-2012_08
Patent number
US08247413B2

Reaction notes

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