4-Morpholinobenzylamine → N-5-isoquinolinyl-N'-[4-(4-morpholinyl)benzyl]urea

HRID 887193

Reaction equation

HRID 887193 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][NH2:14])=[CH:9][CH:8]=2)[CH2:6][CH2:5][O: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]=[CH:21][N:22]=[CH:23]2)=[C:16]=[O:17]>C(OCC)C>[CH:23]1[C:24]2[C:19](=[C:18]([NH:15][C:16]([NH:14][CH2:13][C:10]3[CH:9]=[CH:8][C:7]([N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)=[CH:12][CH:11]=3)=[O:17])[CH:27]=[CH:26][CH:25]=2)[CH:20]=[CH:21][N:22]=1

Participants

4

Reactant 2

HCID 27764584-MorpholinobenzylamineHCID 115863575-Isocyanatoisoquinoline

Product 1

HCID 10248092N-5-isoquinolinyl-N'-[4-(4-morpholinyl)benzyl]urea

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The product from Example 66B (285 mg, 1.48 mmol) in diethyl ether (10 mL) was treated with the product from Example 61A. The mixture was filtered and the filter cake purified by chromatography (95:5 CH2Cl2-MeOH, eluant) to provide that title compound as a white solid. The corresponding di-hydrochloride salt was prepared using methanolic HCl to afford a yellow solid (505 mg, 78%). 1H NMR (300 MHz, DMSO-d6) δ 9.26 (s, 1H), 8.67 (s, 1H), 8.52-8.55 (m, 1H), 8.32 (dd, J=7.8 Hz, 1.1 Hz, 1H), 7.92 (d, J=6.1 Hz, 1H), 7.73 (d, J=8.2 Hz, 1H), 7.60 (m, 1H), 7.23 (d, J=8.8 Hz, 2H), 6.92-6.96 (m, 3H), 4.26 (d, 5.4 Hz, 2H), 3.72-3.75 (m, 4H), 3.06-3.12 (m, 4H); MS (ESI+) m/z 363 (M+H)+.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filter cake purified by chromatography (95:5 CH2Cl2-MeOH, eluant)

Sources & evidence

ORD record
ord-84f8566165734de08f4524d93fdbfc88
Source dataset
uspto-grants-2012_08
Patent number
US08247413B2

Linked notes

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