(Methoxycarbonylsulfamoyl)triethylammonium hydroxide → N-[4-(5-benzyl-[1,3,4]oxadiazol-2-yl)-pyridin-2-yl]benzamide

HRID 714349Notes

Reaction equation

HRID 714349 reaction equation
C(NNC(C1C=CN=C(NC(=O)C2C=CC=CC=2)C=1)=O)(=O)C1C=CC=CC=1.[C:28]1([CH2:34][C:35]([NH:37][NH:38][C:39]([C:41]2[CH:46]=[CH:45][N:44]=[C:43]([NH:47][C:48](=[O:55])[C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[CH:42]=2)=[O:40])=O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[OH-].COC(NS([N+](CC)(CC)CC)(=O)=O)=O>>[CH2:34]([C:35]1[O:40][C:39]([C:41]2[CH:46]=[CH:45][N:44]=[C:43]([NH:47][C:48](=[O:55])[C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[CH:42]=2)=[N:38][N:37]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 3

HCID 11032497(Methoxycarbonylsulfamoyl)triethylammonium hydroxideHCID 67153859N-(4-(2-benzoylhydrazinecarbonyl)pyridin-2-yl)benzamideHCID 67153966N-(4-(2-(2-phenylacetyl)hydrazinecarbonyl)pyridin-2-yl)benzamide

Product 1

HCID 67153788N-[4-(5-benzyl-[1,3,4]oxadiazol-2-yl)-pyridin-2-yl]benzamideYield 17%

Procedure

Following the procedure as described in Example 11, making variations as required to replace N-(4-(2-benzoylhydrazinecarbonyl)pyridin-2-yl)benzamide with N-(4-(2-(2-phenylacetyl)hydrazinecarbonyl)pyridin-2-yl)benzamide to react with (methoxycarbonylsulfamoyl)triethylammonium hydroxide, N-[4-(5-benzyl-[1,3,4]oxadiazol-2-yl)-pyridin-2-yl]benzamide was obtained as a colorless solid in 17% yield: mp 187-189° C.; 1H NMR (300 MHz, CDCl3) δ 9.14 (br s, 1H), 8.94 (br s, 1H), 8.36 (br s, 1H), 7.94 (d, J=7.9 Hz, 2H), 7.73 (br s, 1H), 7.55-7.51 (m, 3H), 7.39-7.20 (m, 5H), 4.29 (s, 2H); 13C NMR (75 MHz, CDCl3) δ 166.6, 166.0, 163.5, 152.4, 148.4, 133.6, 133.4, 132.7, 129.1, 128.9, 128.8, 127.7, 127.4, 116.9, 111.3, 31.9; MS (ES+) m/z 357.2 (M+1).

Sources & evidence

ORD record
ord-4459b50f284946cb9eee221f3e6f1b56
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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