Dimethyl Sulfoxide → (racemic) N-(5-cyano-4-((2-methoxyethyl)amino)pyridin-2-yl)-7-formyl-6-((3-hydroxy-4-methyl-2-oxopiperazin-1-yl)methyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide

HRID 1778113Notes

Reaction equation

HRID 1778113 reaction equation
[C:1]([C:3]1[C:4]([NH:34][CH2:35][CH2:36][O:37][CH3:38])=[CH:5][C:6]([NH:9][C:10]([N:12]2[C:21]3[N:20]=[C:19]([CH:22]=[O:23])[C:18]([CH2:24][N:25]4[CH2:30][CH2:29][N+:28]([O-])([CH3:31])[CH2:27][C:26]4=[O:33])=[CH:17][C:16]=3[CH2:15][CH2:14][CH2:13]2)=[O:11])=[N:7][CH:8]=1)#[N:2].CS(C)=[O:41]>>[C:1]([C:3]1[C:4]([NH:34][CH2:35][CH2:36][O:37][CH3:38])=[CH:5][C:6]([NH:9][C:10]([N:12]2[C:21]3[C:16](=[CH:17][C:18]([CH2:24][N:25]4[CH2:30][CH2:29][N:28]([CH3:31])[CH:27]([OH:41])[C:26]4=[O:33])=[C:19]([CH:22]=[O:23])[N:20]=3)[CH2:15][CH2:14][CH2:13]2)=[O:11])=[N:7][CH:8]=1)#[N:2]

Participants

3

Reactant 2

HCID 679Dimethyl SulfoxideHCID 1180368704-((8-((5-Cyano-4-((2-methoxyethyl)amino)pyridin-2-yl)carbamoyl)-2-formyl-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)methyl)-1-methyl-3-oxopiperazine 1-oxide

Product 1

HCID 118036487(racemic) N-(5-cyano-4-((2-methoxyethyl)amino)pyridin-2-yl)-7-formyl-6-((3-hydroxy-4-methyl-2-oxopiperazin-1-yl)methyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide

Procedure

A solution of 4-((8-((5-cyano-4-((2-methoxyethyl)amino)pyridin-2-yl)carbamoyl)-2-formyl-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)methyl)-1-methyl-3-oxopiperazine 1-oxide (Example 222, 5 mg, 0.01 mmol) in DMSO (1 ml) was stirred at room temperature. After 30 h, the reaction mixture was concentrated and the residue purified by reverse phase chromatography: Atlantis C18 T3 column (3.5 um, 4.6×150 mm, 45° C.), eluting with 1:1 acetonitrile/water (containing 10 mM NH4OAc, 0.02% TFA). The product containing fraction was evaporated to give the title compound as a gray solid.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customthe residue purified by reverse phase chromatography
  3. washAtlantis C18 T3 column (3.5 um, 4.6×150 mm, 45° C.), eluting with 1:1 acetonitrile/water (containing 10 mM NH4OAc, 0.02% TFA)
  4. additionThe product containing fraction
  5. customwas evaporated

Sources & evidence

ORD record
ord-bf8bb4eb53fe4a99856be9fdb2fa355f
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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