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

HRID 2056865Notes

Reaction equation

HRID 2056865 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.[NH2:15][C:16]1[N:17]=[CH:18][C:19]2[C:24]([CH:25]=1)=[C:23]([NH:26][C:27](=[O:32])C(Cl)(Cl)Cl)[CH:22]=[CH:21][CH:20]=2>>[NH2:15][C:16]1[N:17]=[CH:18][C:19]2[C:24]([CH:25]=1)=[C:23]([NH:26][C:27]([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:32])[CH:22]=[CH:21][CH:20]=2

Participants

3

Reactant 2

HCID 2795551(4-Piperidinophenyl)methylamineHCID 22337669N-(3-amino-5-isoquinolinyl)-2,2,2-trichloroacetamide

Product 1

HCID 10248898N-(3-amino-5-isoquinolinyl)-N'-[4-(1-piperidinyl)benzyl]urea

Procedure

The title compound was prepared using the procedure described in Example 1B using 4-(1-piperidinyl)benzylamine and the product from Example 150A instead of 2-(3-fluorophenyl)ethylamine and the product from Example 1A. 1H NMR (300 MHz, DMSO-d6) δ 8.77 (s, 1H), 8.22 (s, 1H), 7.87 (d, 1H, J=8 Hz), 7.46 (d, 1H, J=8 Hz), 7.16 (d, 2H, J=8.4 Hz), 7.07 (t, 1H, J=8 Hz), 6.91 (d, 2H, J=8.4 Hz), 6.82 (t, 1H, J=6 Hz), 6.70 (s, 1H), 5.91 (s, 2H), 4.22 (d, 2H, J=6 Hz), 3.10 (m, 4H), 1.70-1.45 (m, 6H). MS (ESI) 376 (M+H)+. Anal. Calcd for C22H25N5O.0.1H2O: C, 70.04; H, 6.73; N, 18.56. Found: C, 69.66; H, 6.50; N, 18.55.

Sources & evidence

ORD record
ord-733496ad9eb248b199a7ea83bb48777f
Source dataset
uspto-grants-2008_02
Patent number
US07335678B2

Reaction notes

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