Diisopropylethylamine → HCID 75593311, compound
Reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:11][CH2:12][C:13]([OH:15])=O)[CH:4]=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.[NH2:25][CH2:26][CH:27]([OH:39])[CH2:28][N:29]1[CH2:38][CH2:37][C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:30]1.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1>CN(C=O)C>[CH2:30]1[C:31]2[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:37][CH2:38][N:29]1[CH2:28][CH:27]([OH:39])[CH2:26][NH:25][C:13](=[O:15])[CH2:12][O:11][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[N:1]=[CH:2][CH:3]=[CH:4]2Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To a stirred mixture of 2-(quinolin-8-yloxy)acetic acid (100 mg, 0.492 mmol) in DMF (5 mL) was added DIEA (95 mg, 0.738 mmol), 1-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol (100 mg, 0.492 mmol) and BOP-Cl (151 mg, 0.591 mmol). The mixture was stirred at 25° C. for 48 hours then the reaction mixture was quenched by addition of water (20 mL) and extracted with DCM (3×20 mL). The combined organic extracts were washed with brine (20 mL), dried over anhydrous Na2SO4 and concentrated. The residue was then purified by prep-HPLC to afford the desired product (8 mg, Yield: 4%). 1H NMR (400 MHz, MeOD) δ=8.91 (d, J=4.3 Hz, 1H), 8.42 (d, J=8.3 Hz, 1H), 7.69-7.54 (m, 3H), 7.30 (d, J=7.3 Hz, 1H), 7.12-6.96 (m, 4H), 4.78 (s, 2H), 4.18-4.07 (m, 1H), 3.71 (s, 2H), 3.60-3.49 (m, 1H), 3.48-3.40 (m, 1H), 2.89 (d, J=5.8 Hz, 2H), 2.84 (d, J=4.8 Hz, 2H), 2.65-2.61 (m, 2H). LCMS (m/z): 392.2 (M+1).
Workup
- customthe reaction mixture was quenched by addition of water (20 mL)
- extractionextracted with DCM (3×20 mL)
- washThe combined organic extracts were washed with brine (20 mL)
- dry with materialdried over anhydrous Na2SO4
- concentrationconcentrated
- customThe residue was then purified by prep-HPLC
Sources & evidence
- ORD record
- ord-873366c7fca74d248633efc327ca6d43
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08940726B2
Reaction notes
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