1,4-Dioxane hydrochloride → (S)-2-(6-(1-amino-2-(3,5-difluorophenyl)ethyl)-5-bromopyridin-3-yl)isoindoline-1,3-dione hydrochloride

HRID 2170369Notes

Reaction equation

[Br:1][C:2]1[C:3]([C@@H:19]([NH:29]C(=O)OC(C)(C)C)[CH2:20][C:21]2[CH:26]=[C:25]([F:27])[CH:24]=[C:23]([F:28])[CH:22]=2)=[N:4][CH:5]=[C:6]([N:8]2[C:16](=[O:17])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:18])[CH:7]=1.[ClH:37].O1CCOCC1>CO>[ClH:37].[NH2:29][C@H:19]([C:3]1[N:4]=[CH:5][C:6]([N:8]2[C:9](=[O:18])[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:16]2=[O:17])=[CH:7][C:2]=1[Br:1])[CH2:20][C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[C:23]([F:28])[CH:22]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Compound 30E (260 mg, 0.047 mmol) was dissolved in 10 mL of methanol and cooled to 0° C. To it was added 4N HCl/1,4-dioxane (2 ml). The reaction mixture was stirred at room temperature for overnight and concentrated to afford the title product. MS (m/z) 458.00 [M+H]+

Workup

concentrationconcentrated

Sources & evidence

ORD record: ord-3cbdd6b6b9c0416486054b8aba2d0947
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09050344B2

Reaction notes

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