HCID 10264157, compound → HCID 90245254, compound

HRID 2202042Notes

Reaction equation

HRID 2202042 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=1)[C:12]([O:14]C)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:19][CH2:20][C@H:21]([OH:33])[CH2:22][N:23]1[CH2:32][CH2:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24]1>CCO>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:11]([C:12](=[O:14])[NH:19][CH2:20][C@H:21]([OH:33])[CH2:22][N:23]2[CH2:32][CH2:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:24]2)[CH:10]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 10264157HCID 10264157, compoundHCID 25312355(S)-1-Amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol

Product 1

HCID 90245254HCID 90245254, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of methyl 3-((tert-butoxycarbonyl)amino)benzoate (500 mg, 2 mmol) and (S)-1-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol (618 mg, 3 mmol) in EtOH (1 mL) was heated at 120° C. for 3 h in a microwave reactor under N2. The reaction solution was concentrated and the residue was purified by column chromatography to give the title product (500 mg, Yield 58.8%). LCMS (m/z): 426.2 (M+1).

Workup

  1. concentrationThe reaction solution was concentrated
  2. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-74cff24ed52145aca4b64c396880e6ee
Source dataset
uspto-grants-2016_06
Patent number
US09365519B2

Reaction notes

Loading…