1,4-Dioxane hydrochloride → (S)-5-(2-(1-amino-2-(3,5-difluorophenyl)ethyl)-5-(1,3-dioxoisoindolin-2-yl)pyridin-3-yl)-2-fluorobenzamide hydrochloride

HRID 2170363Notes

Reaction equation

HRID 2170363 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:11]2[C:12]([C@@H:28]([NH:38]C(=O)OC(C)(C)C)[CH2:29][C:30]3[CH:35]=[C:34]([F:36])[CH:33]=[C:32]([F:37])[CH:31]=3)=[N:13][CH:14]=[C:15]([N:17]3[C:25](=[O:26])[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:18]3=[O:27])[CH:16]=2)[CH:7]=[CH:8][C:9]=1[F:10])(=[O:3])[NH2:2].[ClH:46].O1CCOCC1>CO>[ClH:46].[NH2:38][C@H:28]([C:12]1[C:11]([C:6]2[CH:7]=[CH:8][C:9]([F:10])=[C:4]([CH:5]=2)[C:1]([NH2:2])=[O:3])=[CH:16][C:15]([N:17]2[C:18](=[O:27])[C:19]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:25]2=[O:26])=[CH:14][N:13]=1)[CH2:29][C:30]1[CH:35]=[C:34]([F:36])[CH:33]=[C:32]([F:37])[CH:31]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 90281443(S)-tert-butyl 1-(3-(3-carbamoyl-4-fluorophenyl)-5-(1,3-dioxoisoindolin-2-yl)pyridin-2-yl)-2-(3,5-difluorophenyl)ethylcarbamate

Product 1

HCID 90281284(S)-5-(2-(1-amino-2-(3,5-difluorophenyl)ethyl)-5-(1,3-dioxoisoindolin-2-yl)pyridin-3-yl)-2-fluorobenzamide hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

(S)-tert-butyl 1-(3-(3-carbamoyl-4-fluorophenyl)-5-(1,3-dioxoisoindolin-2-yl)pyridin-2-yl)-2-(3,5-difluorophenyl)ethylcarbamate (30G, 29 mg, 0.047 mmol) was dissolved in 0.5 mL of methanol and cooled to 0° C. To it was added 4N HCl/1,4-dioxane (0.05 ml). The reaction mixture was stirred at room temperature for 10 minutes and concentrated to afford the title product. MS (m/z) 516.96 [M+H]+.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-80fcfd3a02df4a53895d5fc0d3acb18b
Source dataset
uspto-grants-2015_06
Patent number
US09050344B2

Reaction notes

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