1-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol → HCID 90241009, compound

HRID 1429493Notes

Reaction equation

HRID 1429493 reaction equation
C(O[C:4](=[O:29])[CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1)[N:11]=[CH:10]2)C.[NH2:30][CH2:31][CH:32]([OH:44])[CH2:33][N:34]1[CH2:43][CH2:42][C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH2:35]1>CCO>[CH2:35]1[C:36]2[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:42][CH2:43][N:34]1[CH2:33][CH:32]([OH:44])[CH2:31][NH:30][C:4](=[O:29])[CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH:16]1[CH2:17][CH2:18][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:20][CH2:21]1)[N:11]=[CH:10]2

Participants

4

Reactant 2

HCID 167907201-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-olHCID 90241399HCID 90241399, compound

Product 1

HCID 90241009HCID 90241009, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of tert-butyl 4-(5-(2-ethoxy-2-oxoethoxy)-1H-indazol-1-yl)piperidine-1-carboxylate (100 mg, 0.248 mmol) in EtOH (2 mL) was added 1-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol (102.2 mg, 0.496 mmol) and the mixture was stirred at 120° C. for 2 h in microwave under N2. The mixture was allowed to cool, concentrated under reduced pressure, purified by TLC (Pet.Ether:EtOAc=1:1) to give tert-butyl 4-(5-(2-((3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-hydroxypropyl)amino)-2-oxoethoxy)-1H-indazol-1-yl)piperidine-1-carboxylate (70 mg, yield 50%) as a colorless oil. LCMS (m/z): 564.3 [M+H]+

Workup

  1. temperatureto cool
  2. concentrationconcentrated under reduced pressure
  3. custompurified by TLC (Pet.Ether:EtOAc=1:1)

Sources & evidence

ORD record
ord-5f117bd03cd44178b6e70cd5922d7e03
Source dataset
uspto-grants-2015_01
Patent number
US08940726B2

Reaction notes

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