1,4-Dioxane hydrochloride → 2-amino-2-(4-chlorophenyl)-N-(5-(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)pyridin-3-yl)acetamide

HRID 82119Notes

Reaction equation

HRID 82119 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:32]C(=O)OC(C)(C)C)[C:9]([NH:11][C:12]2[CH:13]=[N:14][CH:15]=[C:16]([C:18]([C:20]3[C:28]4[CH:27]=[N:26][CH:25]=[N:24][C:23]=4[N:22]([CH:29]([CH3:31])[CH3:30])[CH:21]=3)=[O:19])[CH:17]=2)=[O:10])=[CH:4][CH:3]=1.Cl.O1CCOCC1>>[NH2:32][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:9]([NH:11][C:12]1[CH:13]=[N:14][CH:15]=[C:16]([C:18]([C:20]2[C:28]3[CH:27]=[N:26][CH:25]=[N:24][C:23]=3[N:22]([CH:29]([CH3:31])[CH3:30])[CH:21]=2)=[O:19])[CH:17]=1)=[O:10]

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 70856232tert-butyl (1-(4-chlorophenyl)-2-((5-(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)pyridin-3-yl)amino)-2-oxoethyl)carbamate

Product 1

HCID 708179792-amino-2-(4-chlorophenyl)-N-(5-(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)pyridin-3-yl)acetamideYield 8%

Procedure

To tert-butyl (1-(4-chlorophenyl)-2-((5-(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)pyridin-3-yl)amino)-2-oxoethyl)carbamate (Preparation 299, 64 mg, 0.11 mmol) was added 4M HCl/dioxane (5 mL) and the reaction stirred at room temperature for 18 hours. The mixture was evaporated in vacuo and purified by preparative reverse phase HPLC to give the title compound as a beige solid in 8% yield, 4 mg.

Workup

  1. customThe mixture was evaporated in vacuo
  2. custompurified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-af974f211c1f4c598f549ccae4a71d68
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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