1-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol → HCID 90241471, compound

HRID 1429474Notes

Reaction equation

HRID 1429474 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[C:10]([O:17][CH2:18][C:19]([O:21]CC)=O)[CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH2:3][CH2:2]1.[NH2:24][CH2:25][CH:26]([OH:38])[CH2:27][N:28]1[CH2:37][CH2:36][C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:29]1>CCO>[CH2:29]1[C:30]2[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:36][CH2:37][N:28]1[CH2:27][CH:26]([OH:38])[CH2:25][NH:24][C:19](=[O:21])[CH2:18][O:17][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[N:8]=[C:7]([N:4]1[CH2:3][CH2:2][O:1][CH2:6][CH2:5]1)[CH:16]=[CH:15]2

Participants

4

Reactant 2

HCID 167907201-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-olHCID 90237868HCID 90237868, compound

Product 1

HCID 90241471HCID 90241471, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred mixture of ethyl 2-((2-morpholinoquinolin-8-yl)oxy)acetate (100 mg, 0.316 mmol) in EtOH (2 mL) was added 1-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol (65 mg, 0.316 mmol). The mixture was stirred at 120° C. for 0.5 hour under microwave conditions then after evaporation of solvent, the reaction mixture was purified by prep-HPLC to afford the title product (14 mg, Yield 10%). 1H NMR (400 MHz, MeOD) δ=8.04 (d, J=9.3 Hz, 1H), 7.43-7.36 (m, 1H), 7.23-7.16 (m, 3H), 7.10-7.00 (m, 3H), 6.97 (d, J=4.8 Hz, 1H), 4.77 (s, 2H), 3.96 (t, J=6.3 Hz, 1H), 3.87-3.83 (m, 4H), 3.77-3.72 (m, 4H), 3.63-3.53 (m, 2H), 3.52-3.45 (m, 1H), 3.40 (d, J=6.3 Hz, 1H), 2.83 (d, J=5.8 Hz, 2H), 2.75-2.67 (m, 2H), 2.56-2.37 (m, 2H). LCMS (m/z): 477.2 (M+1).

Workup

  1. customafter evaporation of solvent
  2. customthe reaction mixture was purified by prep-HPLC

Sources & evidence

ORD record
ord-84bb225f258148e7918c0caa52bc984b
Source dataset
uspto-grants-2015_01
Patent number
US08940726B2

Reaction notes

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