Ethanol → 3-(benzyloxy)-5-bromo-N-(4-methylthiazol-2-yl)pyridin-2-amine hydrochloride

HRID 1426083Notes

Reaction equation

HRID 1426083 reaction equation
[Cl:1][CH2:2][C:3](=O)[CH3:4].[CH2:6]([O:13][C:14]1[C:15]([NH:21][C:22]([NH2:24])=[S:23])=[N:16][CH:17]=[C:18]([Br:20])[CH:19]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C.C(O)C>O>[ClH:1].[CH2:6]([O:13][C:14]1[C:15]([NH:21][C:22]2[S:23][CH:2]=[C:3]([CH3:4])[N:24]=2)=[N:16][CH:17]=[C:18]([Br:20])[CH:19]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 6571ChloroacetoneHCID 8471TriethylamineHCID 727056401-(3-(Benzyloxy)-5-bromopyridin-2-yl)thiourea

Product 1

HCID 160614653-(benzyloxy)-5-bromo-N-(4-methylthiazol-2-yl)pyridin-2-amine hydrochlorideYield 81.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 1 L round-bottomed flask was charged with 1-chloropropan-2-one (4.833 g, 52.24 mmol), 1-(3-(benzyloxy)-5-bromopyridin-2-yl)thiourea (12.62 g, 37.31 mmol), triethylamine (8.841 mL, 63.43 mmol), and ethanol (30 mL). The reaction mixture was heated to reflux overnight, then poured into water and extracted with methylene chloride. The organic layer was dried over sodium sulfate, filtered, and concentrated to provide 3-(benzyloxy)-5-bromo-N-(4-methylthiazol-2-yl)pyridin-2-amine hydrochloride (11.5 g, 81.9% yield) as a white powder. 1H NMR (d6-DMSO) 8.05 (d, 1H), 7.77 (m, 1H), 7.59 (m, 2H), 7.43 (m, 2H), 7.37 (m, 1H), 6.79 (s, 1H), 5.33 (s, 2H), 2.29 (s, 3H). Mass spectrum (apci) m/z=378.0 (M+H-HCl). Analysis calculated for C16H15BrClN3OS: C, 46.56; H, 3.66; N, 10.18. found: C, 46.56; H, 3.77; N, 10.02.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux overnight
  3. extractionextracted with methylene chloride
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9abea864fa084032b31df8636013a85a
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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