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

HRID 2056812

Reaction equation

HRID 2056812 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-dbfeb5c3d8484b68ba2778d9d9ed79ab
Source dataset
uspto-grants-2008_02
Patent number
US07335678B2

Linked notes

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