Aluminum(III) Chloride → HCID 25012028, compound

HRID 1098816Notes

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 aluminum 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-86a2519e725f4cf88e0c56f524228919
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143290B2

Reaction notes

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