3-Chlorothiophene-2-carbonyl chloride → 3-(4-Aminopyrimidin-5-yl)-5-(3-chloro-thiophen-2-yl)-[1,2,4]-oxadiazole

HRID 2114922Notes

Reaction equation

HRID 2114922 reaction equation
[NH2:1][C:2]1[C:7]([C:8](=[N:10][OH:11])[NH2:9])=[CH:6][N:5]=[CH:4][N:3]=1.[Cl:12][C:13]1[CH:17]=[CH:16][S:15][C:14]=1[C:18](Cl)=O>>[NH2:1][C:2]1[C:7]([C:8]2[N:9]=[C:18]([C:14]3[S:15][CH:16]=[CH:17][C:13]=3[Cl:12])[O:11][N:10]=2)=[CH:6][N:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 27358243-Chlorothiophene-2-carbonyl chlorideHCID 27403554-Amino-pyrimidine-5-amidoxime

Product 1

HCID 98142473-(4-Aminopyrimidin-5-yl)-5-(3-chloro-thiophen-2-yl)-[1,2,4]-oxadiazole

Procedure

The title compound was prepared from 4-amino-pyrimidine-5-amidoxime (50 mg, 0.33 mmol) and 3-chloro-thiophene-2-carbonyl chloride (59 mg, 0.33 mmol), similar to Example 16, and yielded 25 mg (27%) of yellow solid. 1H NMR (CDCl3): 9.18 (s, 1H), 8.69 (s, 1H), 7.66 (d, J=5.22 Hz, 1H), 7.16 (d, J=5.22 Hz, 1H), 5.85 (s, 1H), 3.51 (s, 1H).

Sources & evidence

ORD record
ord-a825870d4c5a48f7be365e6a6d876a94
Source dataset
uspto-grants-2008_10
Patent number
US07435750B2

Reaction notes

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