6-(Benzene sulfonyl amino-methyl)-3-hydroxy-1-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid → 6-(Benzene sulfonyl amino-methyl)-3-hydroxy-1-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid isopropyl amide

HRID 1846902Notes

Reaction equation

HRID 1846902 reaction equation
[CH:1]([NH:4][C:5]([C:7]1[N:8]([CH3:33])[C:9]([CH2:22][NH:23]S(C2C=CC=CC=2)(=O)=O)=[CH:10][C:11](=[O:21])[C:12]=1[O:13]CC1C=CC=CC=1)=[O:6])([CH3:3])[CH3:2].[C:34]1([S:40](C(N)C2N(C)C(C(O)=O)=C(O)C(=O)C=2)(=[O:42])=[O:41])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>>[CH:1]([NH:4][C:5]([C:7]1[N:8]([CH3:33])[C:9]([CH:22]([S:40]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)(=[O:42])=[O:41])[NH2:23])=[CH:10][C:11](=[O:21])[C:12]=1[OH:13])=[O:6])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 867256976-(Benzene sulfonyl amino-methyl)-3-hydroxy-1-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acidHCID 867257606-(Benzenesulfonylamino-methyl)-3-benzyloxy-1-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid isopropyl amide

Product 1

HCID 867257596-(Benzene sulfonyl amino-methyl)-3-hydroxy-1-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid isopropyl amideYield 48.56%

Procedure

6-(Benzene sulfonyl amino-methyl)-3-hydroxy-1-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid isopropyl amide (18-01) (110.0 mg, 48.56%, purified by Prep-HPLC) was synthesized as an off white solid from 6-(benzene sulfonyl amino-methyl)-3-benzyloxy-1-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid isopropyl amide (17-01) (280.0 mg, 0.597 mmol) following the procedure described for 6-(benzene sulfonyl amino-methyl)-3-hydroxy-1-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid (14-01).

Sources & evidence

ORD record
ord-0a193b6ff77b4524b378a172087697cc
Source dataset
uspto-grants-2015_02
Patent number
US08952039B2

Reaction notes

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