Hydroxyamine hydrochloride → HCID 123864132, compound

HRID 2279273Notes

Reaction equation

HRID 2279273 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[S:5][C:6]=1[C:7]1[N:12]=[C:11]2[C:13](=O)[CH2:14][CH2:15][O:16][C:10]2=[CH:9][CH:8]=1.[NH2:24]O.Cl.C[C:28]([O-:30])=O.[K+]>CO>[CH3:28][O:30][N:24]=[C:13]1[C:11]2=[N:12][C:7]([C:6]3[S:5][C:4]([C:18]4[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=4)=[N:3][C:2]=3[CH3:1])=[CH:8][CH:9]=[C:10]2[O:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517044Potassium AcetateHCID 118081840HCID 118081840, compound

Product 1

HCID 123864132HCID 123864132, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-2,3-dihydropyrano[3,2-b]pyridin-4-one (100 mg, 0.31 mmol), compound H2N—OH.HCl (51 mg, 0.62 mmol) and KOAc (61 mg, 0.62 mmol) were suspended in methanol (3 mL) under N2. The reaction mixture was refluxed for 18 hours and purified by chromatography on silica (Ethyl acetate) to get the pure compound as yellow solid (84 mg, 78%). 1H NMR (400 Mz, CDCl3): 2.68 (s, 3H); 2.97 (t, 2H); 4.00 (s, 3H); 4.28 (t, 2H); 7.55-7.46 (m, 2H); 7.72-7.69 (m, 1H); 8.231-8.29 (m, 2H); 8.66-8.65 (m, 1H); 9.13 (s, 1H). Mpt 148-149° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 18 hours
  2. custompurified by chromatography on silica (Ethyl acetate)

Sources & evidence

ORD record
ord-25c0ced5c743476ca08f7d5749791fc0
Source dataset
uspto-grants-2015_09
Patent number
US09133218B2

Reaction notes

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