Ethanol → 5-[2-Hydroxy-3-(9-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-en-7-yl)-propoxy]-3,4-dihydro-1H-quinolin-2-one

HRID 40637Notes

Reaction equation

[O:1]1[CH2:3][C@H:2]1[CH2:4][O:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][C:10](=[O:16])[NH:11]2.[CH:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]=1[N:27]1[CH2:34][C@H:33]2[NH:35][CH2:36][C@@H:28]1[CH2:29][CH:30]=[CH:31][CH2:32]2.C(O)C.CCN(C(C)C)C(C)C>C(Cl)Cl>[OH:1][CH:2]([CH2:3][N:35]1[CH2:36][CH:28]2[N:27]([C:18]3[CH:19]=[CH:20][C:21]4[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:17]=3)[CH2:34][CH:33]1[CH2:32][CH:31]=[CH:30][CH2:29]2)[CH2:4][O:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][C:10](=[O:16])[NH:11]2

Participants

Conditions

Temperature: 95 °C

Procedure

(S)-5-Oxiranylmethoxy-3,4-dihydro-1H-quinolin-2-one (25 mg, 0.114 mmol) and Z-(1S,6S)-7-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-ene (30 mg, 0.114 mmol) were placed in a μW tube with ethanol (2 ml), CH2Cl2 (2 mL), DIPEA (100 μL, 0.576 mmol) and heated to 95° C. for 900 sec. The solvent was evaporated from the reaction mixture and the residue was purified via flash chromatography (gradient 10% to 100% Ethyl acetate/heptane) to yield the title compound as a residue.

Workup

customThe solvent was evaporated from the reaction mixture
customthe residue was purified via flash chromatography (gradient 10% to 100% Ethyl acetate/heptane)

Sources & evidence

ORD record: ord-e36201a9540e4a698b56f21ca4f639ad
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530475B2

Reaction notes

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