1-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol → HCID 90241396, compound

HRID 1429503Notes

Reaction equation

HRID 1429503 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH2:6][O:5][C:4]2[CH:9]=[CH:10][CH:11]=[C:12]([O:13][CH2:14][C:15]([O:17]CC)=O)[C:3]1=2.[NH2:20][CH2:21][CH:22]([OH:34])[CH2:23][N:24]1[CH2:33][CH2:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25]1>CCO>[CH2:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:32][CH2:33][N:24]1[CH2:23][CH:22]([OH:34])[CH2:21][NH:20][C:15](=[O:17])[CH2:14][O:13][C:12]1[C:3]2[N:2]([CH3:1])[C:7](=[O:8])[CH2:6][O:5][C:4]=2[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 167907201-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-olHCID 86729448HCID 86729448, compound

Product 1

HCID 90241396HCID 90241396, compoundYield 27.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A reaction vessel containing a mixture of ethyl 2-(4-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-5-yloxy)acetate (43.0 mg, 0.162 mmol), 1-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol (33.0 mg, 0.163 mmol) and EtOH (0.5 mL) was placed in a microwave reactor and the mixture irradiated at external temperature of 120° C. for 1 h. The reaction mixture was purified in two steps by preparative TLC followed by preparative HPLC to render the title product (19.2 mg, 19% yield)

Workup

  1. additionA reaction vessel containing
  2. customwas placed in a microwave reactor
  3. customthe mixture irradiated at external temperature of 120° C. for 1 h
  4. customThe reaction mixture was purified in two steps by preparative TLC

Sources & evidence

ORD record
ord-1de1819afc67495c9095e62af4668e21
Source dataset
uspto-grants-2015_01
Patent number
US08940726B2

Reaction notes

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