Ethyl (quinolin-8-yloxy)acetate → (S)-N-(2-hydroxy-3-(isoindolin-2-yl)propyl)-2-phenoxyacetamide

HRID 1507016Notes

Reaction equation

HRID 1507016 reaction equation
[NH2:1][CH2:2][C@H:3]([OH:14])[CH2:4][N:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1.N1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][C:23]=2[O:25][CH2:26][C:27](OCC)=[O:28])C=CC=1>CCO>[OH:14][C@H:3]([CH2:4][N:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:2][NH:1][C:27](=[O:28])[CH2:26][O:25][C:23]1[CH:24]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 4379860Ethyl (quinolin-8-yloxy)acetateHCID 60055580(2S)-1-amino-3-(1,3-dihydroisoindol-2-yl)propan-2-ol

Product 1

HCID 86729443(S)-N-(2-hydroxy-3-(isoindolin-2-yl)propyl)-2-phenoxyacetamideYield 31%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (S)-1-amino-3-(isoindolin-2-yl)propan-2-ol (100 mg, 0.52 mmol), ethyl 2-(quinolin-8-yloxy)acetate (120 mg, 0.52 mmol) in EtOH (1 mL) was heated under microwave conditions at 120° C. for 0.5 h. The reaction mixture was concentrated and purified by preparative HPLC purification. (60 mg, yield 31%) MS (ESI+) e/z: 378.1 [M+1]+. 1H NMR (MeOD, 400 MHz), δ ppm: 8.93-8.88 (m, 1H), 8.44-8.38 (m, 1H), 7.66-7.57 (m, 3H), 7.34-7.29 (m, 1H), 7.24-7.14 (m, 4H), 4.82-4.79 (m, 2H), 4.08-4.03 (m, 1H), 3.99 (s, 4H), 3.60-3.55 (m, 1H), 3.46-3.40 (m, 1H), 2.91-2.85 (m, 1H), 2.8-2.78 (m, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by preparative HPLC purification

Sources & evidence

ORD record
ord-b7d1a1dd1f964cdba2e1b0f45d0efa6d
Source dataset
uspto-grants-2015_12
Patent number
US09221794B2

Reaction notes

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