Aluminum(III) Chloride → HCID 25012028, compound

HRID 13051Notes

Reaction equation

[F:1][C:2]([F:35])([F:34])[C:3]([NH:5][C@@H:6]([CH3:33])[C@H:7]([O:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[N:22]([C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=1)[N:21]=[CH:20]2)[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14]C)[CH:9]=1)=[O:4].[Cl-].[Al+3].[Cl-].[Cl-]>CC1C=CC=CC=1>[F:34][C:2]([F:1])([F:35])[C:3]([NH:5][C@@H:6]([CH3:33])[C@H:7]([O:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[N:22]([C:26]1[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=1)[N:21]=[CH:20]2)[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[CH:9]=1)=[O:4]

Participants

Conditions

Temperature: 40 °C

Procedure

To a stirred solution of 2,2,2-trifluoro-N-((1R,2S)-1-(1-(4-fluorophenyl)-1H-indazol-5-yloxy)-1-(3-methoxyphenyl)propan-2-yl)acetamide (Example 6, 10 mg, 20 μmol) in methylbenzene (1 ml) was added dodecanethiole (1 ml), followed with anhydrous aluminium chloride (5.3 mg, 40 μmol). The mixture was stirred at 40° C. for 1 h. Methylbenzene was removed in vacuo, the solution in dodecanethiole was diluted with n-heptane (10 ml). Oily precipitate has formed, which was washed with heptane, dried in vacuo, and dissolved in acetonitrile/water mixture. The crude product was purified by preparative HPLC afforded 4 mg of product as a white solid (42%).

Workup

customMethylbenzene was removed in vacuo
additionthe solution in dodecanethiole was diluted with n-heptane (10 ml)
customOily precipitate has formed
washwhich was washed with heptane
customdried in vacuo
dissolutiondissolved in acetonitrile/water mixture
customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record: ord-0099cb2593d64fb4bcefdf71a5a06ba3
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728030B2

Reaction notes

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