1-Amino-3-(isoindolin-2-yl)propan-2-ol → 2-(2-(N,N-dimethylsulfamoyl)phenoxy)-N-(2-hydroxy-3-(isoindolin-2-yl)propyl)acetamide

HRID 1507040Notes

Reaction equation

[CH3:1][N:2]([CH3:19])[S:3]([C:6]1[CH:18]=[CH:17][CH:16]=[CH:15][C:7]=1[O:8][CH2:9][C:10]([O:12]CC)=O)(=[O:5])=[O:4].[NH2:20][CH2:21][CH:22]([OH:33])[CH2:23][N:24]1[CH2:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25]1>CCO>[CH3:19][N:2]([CH3:1])[S:3]([C:6]1[CH:18]=[CH:17][CH:16]=[CH:15][C:7]=1[O:8][CH2:9][C:10]([NH:20][CH2:21][CH:22]([OH:33])[CH2:23][N:24]1[CH2:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25]1)=[O:12])(=[O:4])=[O:5]

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of ethyl 2-(2-(N,N-dimethylsulfamoyl)phenoxy)acetate (100 mg, 0.35 mmol) in EtOH (1 mL) was added 1-amino-3-(isoindolin-2-yl)propan-2-ol (66.8 mg, 0.35 mmol). The reaction mixture was heated under microwave conditions at 120° C. for 0.5 h. The material was concentrated and purified by preparative HPLC purification. (20 mg, yield 13%) MS (ESI+) e/z: 434.1 [M+1]+. 1H NMR (MeOD, 400 MHz), δ ppm: 7.85 (dd, J=7.78, 1.51 Hz, 1H), 7.70-7.61 (m, 1H), 7.27-7.16 (m, 6H), 4.75 (s, 2H), 4.05-3.91 (m, 5H), 3.55 (dd, J=13.68, 4.89 Hz, 1H), 3.40-3.35 (m, 1H), 2.92-2.77 (m, 8H).

Workup

concentrationThe material was concentrated
custompurified by preparative HPLC purification

Sources & evidence

ORD record: ord-3d0c17c48fe742a8b9253510893ca964
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221794B2

Reaction notes

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