Isopropanol → HCID 57970196, compound

HRID 1666639Notes

Reaction equation

[C:1]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]([N:10]1[CH2:14][CH2:13][C@H:12]([NH:15][C:16]2[CH:25]=[C:24](Cl)[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=2)[CH2:11]1)=[O:9].C(OC([N:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1)=O)(C)(C)C.C(N(CC)CC)C.C(O)(C)C>C(Cl)(Cl)Cl.O>[C:1]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]([N:10]1[CH2:14][CH2:13][C@H:12]([NH:15][C:16]2[CH:25]=[C:24]([N:40]3[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]3)[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=2)[CH2:11]1)=[O:9]

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 2-biphenyl-2-yl-1-((S)-3-(4-chloroquinolin-2-ylamino)pyrrolidin-1-yl)ethanone (0.43 g), 1-(t-butoxycarbonyl)piperazine (0.18 g), triethylamine (0.17 g), and isopropanol (1.3 mL) was heated at 180° C. in a microwave reaction apparatus for 5 h. The reaction mixture was diluted with chloroform and water, and then the aqueous layer was extracted with chloroform and dried with anhydrous magnesium sulfate. The desiccant was removed by filtration, then the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform/a solution of 2 M ammonia in methanol=9:1) and then solidified in diethyl ether to obtain the title compound (22 mg).

Workup

extractionthe aqueous layer was extracted with chloroform
dry with materialdried with anhydrous magnesium sulfate
customThe desiccant was removed by filtration
concentrationthe filtrate was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (chloroform/a solution of 2 M ammonia in methanol=9:1) and

Sources & evidence

ORD record: ord-136a8f24ff6f4a8a972d760781949d0e
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044068B2

Reaction notes

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