Lithium Hydroxide → 6-(6-(3-ethylureido)-4-(4-(1-methyl-1H-pyrazol-4-yl)thiazol-2-yl)pyridin-3-yl)-1-((1-methyl-1H-imidazol-4-yl)methyl)-4-oxo-1,4-dihydro-1,7-naphthyridine-3-carboxylic acid

HRID 1047135Notes

Reaction equation

HRID 1047135 reaction equation
[Li+].[OH-].[CH2:3]([NH:5][C:6](=[O:48])[NH:7][C:8]1[N:13]=[CH:12][C:11]([C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][N:23]=2)[N:20]([CH2:24][C:25]2[N:26]=[CH:27][N:28]([CH3:30])[CH:29]=2)[CH:19]=[C:18]([C:31]([O:33]CC)=[O:32])[C:17]3=[O:36])=[C:10]([C:37]2[S:38][CH:39]=[C:40]([C:42]3[CH:43]=[N:44][N:45]([CH3:47])[CH:46]=3)[N:41]=2)[CH:9]=1)[CH3:4].C1COCC1>CO>[CH2:3]([NH:5][C:6](=[O:48])[NH:7][C:8]1[N:13]=[CH:12][C:11]([C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][N:23]=2)[N:20]([CH2:24][C:25]2[N:26]=[CH:27][N:28]([CH3:30])[CH:29]=2)[CH:19]=[C:18]([C:31]([OH:33])=[O:32])[C:17]3=[O:36])=[C:10]([C:37]2[S:38][CH:39]=[C:40]([C:42]3[CH:43]=[N:44][N:45]([CH3:47])[CH:46]=3)[N:41]=2)[CH:9]=1)[CH3:4]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 68749575ethyl 6-(6-(3-ethylureido)-4-(4-(1-methyl-1H-pyrazol-4-yl)thiazol-2-yl)pyridin-3-yl)-1-((1-methyl-1H-imidazol-4-yl)methyl)-4-oxo-1,4-dihydro-1,7-naphthyridine-3-carboxylate

Product 1

HCID 687500606-(6-(3-ethylureido)-4-(4-(1-methyl-1H-pyrazol-4-yl)thiazol-2-yl)pyridin-3-yl)-1-((1-methyl-1H-imidazol-4-yl)methyl)-4-oxo-1,4-dihydro-1,7-naphthyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2N LiOH (1 mL) was added to a mixture of ethyl 6-(6-(3-ethylureido)-4-(4-(1-methyl-1H-pyrazol-4-yl)thiazol-2-yl)pyridin-3-yl)-1-((1-methyl-1H-imidazol-4-yl)methyl)-4-oxo-1,4-dihydro-1,7-naphthyridine-3-carboxylate, 86.3 mg, 0.14 mmol) in MeOH (imp and THF (1 mL). The resulting solution was stirred at room temperature for two hours. The solvent was removed and the residue was diluted with water and acidified with 1N HCl. The precipitated product was collected by filtration and washed with water and dried (60 mg).

Workup

  1. customThe solvent was removed
  2. additionthe residue was diluted with water
  3. filtrationThe precipitated product was collected by filtration
  4. washwashed with water
  5. customdried (60 mg)

Sources & evidence

ORD record
ord-678d3bc7dc1f49c39ca21146fd728831
Source dataset
uspto-grants-2013_10
Patent number
US08569484B2

Reaction notes

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