Isoxazole-5-carbonyl chloride → HCID 86583850, compound

HRID 2186624Notes

Reaction equation

HRID 2186624 reaction equation
[O:1]1[C:5]([C:6]2[N:7]=[C:8]([C:11]3[C:15](=[CH2:16])[S:14][CH:13]([C:17]([O:19][CH3:20])=[S:18])[CH:12]=3)[S:9][CH:10]=2)=[CH:4][CH:3]=[N:2]1.NC(=S)C1C=C(C(OC)=S)SC=1C.BrCC(C1ON=CC=1)=O.O1C(C(Cl)=O)=CC=N1>>[O:1]1[C:5]([C:6]2[N:7]=[C:8]([C:11]3[CH:12]=[C:13]([C:17]([O:19][CH3:20])=[S:18])[S:14][C:15]=3[CH3:16])[S:9][CH:10]=2)=[CH:4][CH:3]=[N:2]1

Participants

5

Reactant 4

HCID 2736707Isoxazole-5-carbonyl chlorideHCID 185372592-Bromo-1-(1,2-oxazol-5-yl)ethan-1-oneHCID 86583815Methyl 4-(aminothioxomethyl)-5-methylthiothiophene-2-carboxylateHCID 131723303HCID 131723303, compound

Product 1

HCID 86583850HCID 86583850, compoundYield 83%

Procedure

Methyl 4-(4-isoxazol-5-yl(1,3-thiazol-2-yl))-5-methlylthiothiophene-2-carboxylate: Methyl 4-(aminothioxomethyl)-5-methylthiothiophene-2-carboxylate (872 mg, 2.51 mmol) was allowed to react with 2-bromo-1-isoxazol-5-ylethan-1-one (737 mg, prepared from isoxazole-5-carbonyl chloride [Maybridge Chemicals, Cornwall, UK] as described in Example 177, step (a) as described in Example 154, step (a) to give 704 mg (83% yield) of methyl 4-(4-isoxazol-5-yl(1,3-thiazol-2-yl))-5-methylthiothiophene-2-carboxylate. 1H NMR (DMSO-d6, 300 MHz) δ 2.75 (s, 3H), 3.85 (s, 3H), 6.93 (d, 1H, J=1.8 Hz), 8.22 (s, 1H), 8.38 (s, 1H), 8.70 (d, 1H, J=1.8 Hz).

Sources & evidence

ORD record
ord-f4f0858aa0224a14b0e9b99a53093fc3
Source dataset
uspto-grants-2002_06
Patent number
US06403633B2

Reaction notes

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