Triethylamine → N-[5-[2-[(2E)-2-amino-2-hydroxyiminoethyl]-1,3-thiazol-4-yl]-4-methyl-1,3-thiazol-2-yl]acetamide
Reaction equation
[C:1]([CH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9]2[S:13][C:12]([NH:14][C:15](=[O:17])[CH3:16])=[N:11][C:10]=2[CH3:18])[N:8]=1)#[N:2].Cl.[NH2:20][OH:21].C(N(CC)CC)C>O1CCOCC1>[NH2:2]/[C:1](=[N:20]/[OH:21])/[CH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9]2[S:13][C:12]([NH:14][C:15](=[O:17])[CH3:16])=[N:11][C:10]=2[CH3:18])[N:8]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
N-[2-(cyanomethyl)-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl]acetamide, Compound (3) (50 mg; 0.18 mmol; 1 eq.), is dissolved in dioxane (10 ml). Hydroxylamine hydrochloride (15 mg; 0.22 mmol; 1.20 eq.) and N,N-diethylethanamine (0.03 ml; 0.22 mmol; 1.20 eq.) are added and reaction mixture is heated at 80° C. overnight. Reaction mixture is cooled down and dioxane evaporated. The residue is taken up in EtOAc and washed several times with water (3×10 mL). The organic phases are dried over MgSO4, filtrated and evaporated. Crude material is purified by flash chromatography on silica gel (cyclohexane/ethylacetate, 50/50), affording the title compound as an oil (50 mg; 95%).
Workup
- customreaction mixture
- customReaction mixture
- temperatureis cooled down
- customdioxane evaporated
- washwashed several times with water (3×10 mL)
- dry with materialThe organic phases are dried over MgSO4
- filtrationfiltrated
- customevaporated
- customCrude material is purified by flash chromatography on silica gel (cyclohexane/ethylacetate, 50/50)
Sources & evidence
- ORD record
- ord-cc3c531350d6471c8bc7c7a236f1bd47
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07799814B2
Reaction notes
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