1-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol → HCID 90241509, compound

HRID 1429478Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:19]=[CH:18][CH:17]=[CH:16][C:8]=2[O:9][CH2:10][C:11]([O:13]CC)=O)[CH2:3][CH2:2]1.[NH2:20][CH2:21][CH:22]([OH:34])[CH2:23][N:24]1[CH2:33][CH2:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25]1>CCO>[CH2:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:32][CH2:33][N:24]1[CH2:23][CH:22]([OH:34])[CH2:21][NH:20][C:11](=[O:13])[CH2:10][O:9][C:8]1[CH:16]=[CH:17][CH:18]=[CH:19][C:7]=1[N:4]1[CH2:3][CH2:2][O:1][CH2:6][CH2:5]1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of ethyl 2-(2-morpholinophenoxy)acetate (53 mg, 0.2 mmol) and 1-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol (41 mg, 0.2 mmol) in EtOH (1 mL) was stirred at 120° C. over microwave for 30 min. The solvent was removed by concentration and the crude product was purified by prep-HPLC separation to afford product the desired title compound (8.0 mg, Yield 10%). 1H NMR (400 MHz, MeOD): 7.09-6.98 (m, 8H), 4.64 (s, 2H), 3.95 (br.s, 1H), 3.89-3.87 (m, 4H), 3.63-3.46 (m, 2H), 3.33-3.30 (m, 1H), 3.07-3.03 (m, 4H), 2.88 (dd, J=6.0 Hz, 2H), 2.77 (dd, J=6.0 Hz, 2H), 2.49 (d, J=6.0 Hz, 2H). LCMS (m/z): 426.2 (M+1).

Workup

customThe solvent was removed by concentration
customthe crude product was purified by prep-HPLC separation

Sources & evidence

ORD record: ord-bb7527c071204721bc5fd1dea37c874b
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940726B2

Reaction notes

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