Diisopropylethylamine → (S)-1-(7-Chloro-quinolin-4-yloxy)-3-[9-(9H-fluoren-2-yl)-7,9-diaza-bicyclo[4.2.2]dec-3-en-7-yl]-propan-2-ol

HRID 40636Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:12][CH2:13][C@@H:14]3[CH2:16][O:15]3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[CH:17]1[C:29]2[CH2:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]=2[CH:20]=[CH:19][C:18]=1[N:30]1[CH2:37][C@H:36]2[NH:38][CH2:39][C@@H:31]1[CH2:32][CH:33]=[CH:34][CH2:35]2.CCN(C(C)C)C(C)C>C(O)C>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:12][CH2:13][C@@H:14]([OH:15])[CH2:16][N:38]3[CH2:39][CH:31]4[N:30]([C:18]5[CH:19]=[CH:20][C:21]6[C:22]7[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=7)[CH2:28][C:29]=6[CH:17]=5)[CH2:37][CH:36]3[CH2:35][CH:34]=[CH:33][CH2:32]4)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 95 °C

Procedure

(S)-7-Chloro-4-oxiranylmethoxy-quinoline (20 mg, 0.084 mmol) and Z-(1S,6S)-7-(9H-fluoren-2-yl)-7,9-diaza-bicyclo[4.2.2]dec-3-ene (22 mg, 0.073 mmol) were placed in a μW tube with ethanol (3 ml), DIPEA (15 μL, 0.086 mmol) and heated to 95° C. for 900 sec. The solvent was evaporated from the reaction mixture and the residue was purified via reverse phase chromatography (gradient 20% to 90% CH3CN/water for 12 min) to yield the title compound as a residue.

Workup

customThe solvent was evaporated from the reaction mixture
customthe residue was purified via reverse phase chromatography (gradient 20% to 90% CH3CN/water for 12 min)

Sources & evidence

ORD record: ord-fe885eded4c44e909d54c1a60392fbc1
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530475B2

Reaction notes

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