Pyridine → N-(5-{5-[(hydroxyimino)methyl]-2-thienyl}-4-methyl-1,3-thiazol-2-yl)acetamide

HRID 1364494Notes

Reaction equation

C(C1SC(C2SC(NC(=O)C)=C(C)N=2)=CC=1)=O.[CH:18]([C:20]1[S:24][C:23]([C:25]2[S:29][C:28]([NH:30][C:31](=[O:33])[CH3:32])=[N:27][C:26]=2[CH3:34])=[CH:22][CH:21]=1)=O.Cl.[NH2:36][OH:37].N1C=CC=CC=1>C1COCC1.C(O)C>[OH:37][N:36]=[CH:18][C:20]1[S:24][C:23]([C:25]2[S:29][C:28]([NH:30][C:31](=[O:33])[CH3:32])=[N:27][C:26]=2[CH3:34])=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 70 °C

Procedure

N-[2-(5-Formyl-thiophen-2-yl)-4-methyl-thiazol-5-yl]-acetamide, Compound (1) (104 mg; 0.39 mmol; 1 eq.), is dissolved in a THF/Ethanol 1:1 mixture (10 ml) at room temperature. Hydroxylamine hydrochloride (275 mg; 3.9 mmol; 10 eq.) and pyridine (310 μl; 3.9 mmol; 10.0 eq.) are added and reaction mixture is heated at 70° C. for 30 minutes. Reaction mixture is cooled down to room temperature and solvents are evaporated. The crude material is dissolved in dichloromethane and filtrated through a small silica cartridge, affording Compound (14) as mixture of oxime isomers, a yellow solid (55 mg; 55%). 1H NMR (MeOH-d4, 300 MHz) δ 2.25 (s, 3H), 2.50 (s, 3H), 6.65 (s, 1H), 7.12 (d, J=6 Hz, 1H), 7.40 (d, J=6 Hz, 1H), 7.72 (s, 1H). M−(ESI): 280.36; M+(ESI): 282.40. HPLC, Rt: 2.64 min (purity: 87.8%).

Workup

customreaction mixture
customReaction mixture
temperatureis cooled down to room temperature
customsolvents are evaporated
dissolutionThe crude material is dissolved in dichloromethane
filtrationfiltrated through a small silica cartridge

Sources & evidence

ORD record: ord-6986cec4b8cc4d4d9744d24ab1626345
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07888379B2

Reaction notes

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