Hydrochloric Acid → (S)-3-(6-(2-aminopropoxyl)pyridin-2-ylamino)-5-bromo-1-methylpyridin-2(1H)-one hydrochloride

HRID 1774644Notes

Reaction equation

HRID 1774644 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[N:16]=[C:15]([O:17][CH2:18][C@@H:19]([NH:21]C(=O)OC(C)(C)C)[CH3:20])[CH:14]=[CH:13][CH:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[ClH:29]>C(Cl)Cl>[ClH:29].[NH2:21][C@@H:19]([CH3:20])[CH2:18][O:17][C:15]1[N:16]=[C:11]([NH:10][C:4]2[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=[C:2]([Br:1])[CH:3]=2)[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118117363(S)-tert-butyl 1-(6-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)pyridin-2-yloxy)propan-2-ylcarbamate

Product 1

HCID 118117014(S)-3-(6-(2-aminopropoxyl)pyridin-2-ylamino)-5-bromo-1-methylpyridin-2(1H)-one hydrochlorideYield 85.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 107b (550 mg, 1.21 mmol) in DCM (10 mL) was treated with HCl (4 M in dioxone, 3 mL, 12 mmol). The reaction mixture was stirred at rt for 2 h and quenched with sat. Na2CO3, extracted with DCM. The combined extracts were dried over Na2SO4, filtered and concentrated to give 107c (400 mg, 1.03 mmol) as brown solid. MS-ESI: [M+H]+ 352.9

Workup

  1. customquenched with sat. Na2CO3
  2. extractionextracted with DCM
  3. dry with materialThe combined extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d1ca42179832462994ec2f6d11a629da
Source dataset
uspto-grants-2016_02
Patent number
US09260415B2

Reaction notes

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