Hydrochloric Acid → 5-bromo-1-methyl-3-(6-(2-(methylamino)ethoxy)pyridin-2-ylamino)pyridin-2(1H)-one hydrochloride

HRID 1774657Notes

Reaction equation

HRID 1774657 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[N:16]=[C:15]([O:17][CH2:18][CH2:19][N:20](C)[C:21](=O)OC(C)(C)C)[CH:14]=[CH:13][CH:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[ClH:29]>>[ClH:29].[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:12]=[CH:13][CH:14]=[C:15]([O:17][CH2:18][CH2:19][NH:20][CH3:21])[N:16]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 118116879Tert-butyl 2-(6-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)pyridin-2-yloxy)ethyl(methyl)carbamate

Product 1

HCID 1181164835-bromo-1-methyl-3-(6-(2-(methylamino)ethoxy)pyridin-2-ylamino)pyridin-2(1H)-one hydrochlorideYield 85.1%

Procedure

A mixture of 112c (900 mg, 1.99 mmol) in HCl (5 mL, 4 M in 1,4-dioxane, 20 mmol) was stirred at rt for 2 h. The reaction mixture was concentrated to give 5-bromo-1-methyl-3-(6-(2-(methylamino)ethoxy)pyridin-2-ylamino)pyridin-2(1H)-one hydrochloride 112d (660 mg, 85%) as yellow solid. This material was used for next step directly. ESI-LCMS: m/z=354.9 (free base)

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-3c2b9193eb804b8eacb1498edc8f0e12
Source dataset
uspto-grants-2016_02
Patent number
US09260415B2

Reaction notes

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