5-Methylimidazo(1,5-a)pyridine → (6R,7R)-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetyl]amino]-3-[(5-methylimidazo[1,5-a]pyridin-2-ium-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 1607310Notes

Reaction equation

HRID 1607310 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4](/[C:7](=[N:31]/[O:32][CH2:33][CH3:34])/[C:8]([NH:10][C@@H:11]2[C:29](=[O:30])[N:13]3[C:14]([C:26]([OH:28])=[O:27])=[C:15]([CH2:18]OC(=O)CC(=O)C)[CH2:16][S:17][C@H:12]23)=[O:9])[N:3]=1.[CH3:35][C:36]1[N:41]2[CH:42]=[N:43][CH:44]=[C:40]2[CH:39]=[CH:38][CH:37]=1>>[NH2:1][C:2]1[S:6][N:5]=[C:4](/[C:7](=[N:31]/[O:32][CH2:33][CH3:34])/[C:8]([NH:10][C@@H:11]2[C:29](=[O:30])[N:13]3[C:14]([C:26]([O-:28])=[O:27])=[C:15]([CH2:18][N+:43]4[CH:44]=[C:40]5[CH:39]=[CH:38][CH:37]=[C:36]([CH3:35])[N:41]5[CH:42]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:3]=1

Participants

3

Reactant 2

HCID 122109855-Methylimidazo(1,5-a)pyridineHCID 15575218(6R,7R)-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetyl]amino]-8-oxo-3-(3-oxobutanoyloxymethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Product 1

HCID 14124186(6R,7R)-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetyl]amino]-3-[(5-methylimidazo[1,5-a]pyridin-2-ium-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Procedure

By the procedure of Example 1, 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-ethoxyiminoacetamido]-3-(3-oxobutyryloxymethyl)-3-cephem-4-carboxylic acid is reacted with 5-methylimidazo[1,5-a]pyridine to give the title compound.

Sources & evidence

ORD record
ord-d665bc3020274d799d3f8f6ee0e0c4d4
Source dataset
uspto-grants-1989_09
Patent number
US04864022

Reaction notes

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