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

HRID 887193

반응식

HRID 887193 반응식
[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

참가 물질

4

반응물 2

HCID 27764584-MorpholinobenzylamineHCID 115863575-Isocyanatoisoquinoline

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-84f8566165734de08f4524d93fdbfc88
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08247413B2

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