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

HRID 1507034Notes

Reaction equation

[CH3:1][S:2]([C:5]1[CH:17]=[CH:16][CH:15]=[CH:14][C:6]=1[O:7][CH2:8][C:9]([O:11]CC)=O)(=[O:4])=[O:3].[NH2:18][CH2:19][CH:20]([OH:31])[CH2:21][N:22]1[CH2:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23]1>CCO>[OH:31][CH:20]([CH2:21][N:22]1[CH2:23][C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:30]1)[CH2:19][NH:18][C:9](=[O:11])[CH2:8][O:7][C:6]1[CH:14]=[CH:15][CH:16]=[CH:17][C:5]=1[S:2]([CH3:1])(=[O:3])=[O:4]

Participants

Conditions

Temperature: 120 °C

Procedure

Ethyl 2-(2-(methylsulfonyl)phenoxy)acetate (50 mg, 0.19 mmol) and 1-amino-3-(isoindolin-2-yl)propan-2-ol (36 mg, 0.19 mmol) were dissolved in EtOH (1 mL) and heated under microwave conditions at 120° C. 0.5 h. The reaction mixture was concentrated and purified by preparative HPLC purification. (11 mg, yield 14%) MS (ESI+) e/z: 405.2 [M+1]+. 1H NMR (MeOD, 400 MHz), δ ppm: 7.98-7.91 (m, 1H), 7.76-7.69 (m, 1H), 7.33-7.24 (m, 2H), 7.21 (d, J=2.76 Hz, 4H), 4.86-4.80 (m, 2H), 4.01-3.97 (m, 4H), 3.97-3.91 (m, 1H), 3.57-3.50 (m, 1H), 3.39-3.35 (m, 1H), 3.30 (s, 3H), 2.86-2.81 (m, 1H), 2.81-2.74 (m, 1H).

Workup

custom0.5 h
concentrationThe reaction mixture was concentrated
custompurified by preparative HPLC purification

Sources & evidence

ORD record: ord-7d5e44fc7093409eb25ce5a47fc13227
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221794B2

Reaction notes

Loading…