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

HRID 2056882

Reaction equation

HRID 2056882 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][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:12][CH2:11][C:10]3[CH:9]=[CH:8][C:7]([N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)=[CH:14][CH:13]=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 172B (285 mg, 1.48 mmol) in diethyl ether (10 mL) was treated with an ethereal solution of 5-isocyanatoisoquinoline, causing a white precipitate to form. This precipitate was collected by filtration and purified by chromatography (95:5 CH2Cl2-MeOH, eluant) to provide the title compound. The corresponding di-hydrochloride salt was prepared using methanolic HCl to afford a yellow solid. 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. customto form
  2. filtrationThis precipitate was collected by filtration
  3. custompurified by chromatography (95:5 CH2Cl2-MeOH, eluant)

Sources & evidence

ORD record
ord-6ab3b6d4203446938b4d0a73c39e4ea1
Source dataset
uspto-grants-2008_02
Patent number
US07335678B2

Linked notes

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