6-(2-Oxooxazolidin-3-yl)nicotinic acid methyl ester → 3-{5-[4-(3,5,6-Trimethylpyridin-2-yl)piperazine-1-carbonyl]pyridin-2-yl}oxazolidin-2-one

HRID 1804313Notes

Reaction equation

HRID 1804313 reaction equation
CO[C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][O:12][C:11]2=[O:15])=[N:6][CH:5]=1.Cl.[CH3:18][C:19]1[C:20]([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[N:21][C:22]([CH3:26])=[C:23]([CH3:25])[CH:24]=1>>[CH3:18][C:19]1[C:20]([N:27]2[CH2:28][CH2:29][N:30]([C:3]([C:4]3[CH:9]=[CH:8][C:7]([N:10]4[CH2:14][CH2:13][O:12][C:11]4=[O:15])=[N:6][CH:5]=3)=[O:16])[CH2:31][CH2:32]2)=[N:21][C:22]([CH3:26])=[C:23]([CH3:25])[CH:24]=1

Participants

3

Reactant 2

HCID 584844956-(2-Oxooxazolidin-3-yl)nicotinic acid methyl esterHCID 673810521-(3,5,6-Trimethylpyridin-2-yl)piperazine hydrochloride

Product 1

HCID 584845093-{5-[4-(3,5,6-Trimethylpyridin-2-yl)piperazine-1-carbonyl]pyridin-2-yl}oxazolidin-2-oneYield 21.4%

Procedure

By reaction and treatment in the same manner as in Example 63 and using 6-(2-oxooxazolidin-3-yl)nicotinic acid methyl ester (250 mg) described in Preparation Example 138 and 1-(3,5,6-trimethylpyridin-2-yl)piperazine hydrochloride (328 mg) described in Preparation Example 52 after neutralization and conversion to a free form, the title compound (95 mg) was obtained.

Workup

  1. customBy reaction and treatment in the same manner as in Example 63
  2. customdescribed in Preparation Example 52 after neutralization and conversion to a free form

Sources & evidence

ORD record
ord-991e4ba0dd4146118d756ce55efd46ae
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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