6-(Benzene sulfonyl amino-methyl)-3-hydroxy-1-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid → 6-[(3-Chloro-benzenesulfonylamino)-methyl]-3-hydroxy-1-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid

HRID 1846871Notes

Reaction equation

HRID 1846871 reaction equation
C([O:8][C:9]1[C:14](=[O:15])[CH:13]=[C:12]([CH2:16][NH:17][S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=2)(=[O:20])=[O:19])[N:11]([CH3:28])[C:10]=1[C:29]([OH:31])=[O:30])C1C=CC=CC=1.C1(S(C(N)C2N(C)C(C(O)=O)=C(O)C(=O)C=2)(=O)=O)C=CC=CC=1>>[Cl:27][C:23]1[CH:22]=[C:21]([S:18]([NH:17][CH2:16][C:12]2[N:11]([CH3:28])[C:10]([C:29]([OH:31])=[O:30])=[C:9]([OH:8])[C:14](=[O:15])[CH:13]=2)(=[O:19])=[O:20])[CH:26]=[CH:25][CH:24]=1

Participants

3

Reactant 2

HCID 867256976-(Benzene sulfonyl amino-methyl)-3-hydroxy-1-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acidHCID 867257283-Benzyloxy-6-[(3-chloro-benzenesulfonylamino)-methyl]-1-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid

Product 1

HCID 867257296-[(3-Chloro-benzenesulfonylamino)-methyl]-3-hydroxy-1-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acidYield 52.7%

Procedure

6-[(3-Chloro-benzenesulfonylamino)-methyl]-3-hydroxy-1-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid (14-05) (170.0 mg, 52.67%) was synthesized as an off white solid from 3-benzyloxy-6-[(3-chloro-benzenesulfonylamino)-methyl]-1-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid (13-05) (400.0 mg, 0.866 mmol) following the procedure described for 6-(benzenesulfonylamino-methyl)-3-hydroxy-1-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid (14-01).

Sources & evidence

ORD record
ord-e02b763280f441caa077ebe08b62918a
Source dataset
uspto-grants-2015_02
Patent number
US08952039B2

Reaction notes

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