Tetrahydrofuran → 3-{[1-Benzyl-3-(2-dimethylamino-pyrimidin-5-yl)-5-hydroxy-2-oxo-1,2-dihydro-[1,7]naphthyridine-6-carbonyl]-amino}-propionic acid

HRID 1410928Notes

Reaction equation

HRID 1410928 reaction equation
C[O:2][C:3](=[O:37])[CH2:4][CH2:5][NH:6][C:7]([C:9]1[C:10]([OH:36])=[C:11]2[C:16](=[CH:17][N:18]=1)[N:15]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14](=[O:26])[C:13]([C:27]1[CH:28]=[N:29][C:30]([N:33]([CH3:35])[CH3:34])=[N:31][CH:32]=1)=[CH:12]2)=[O:8].[OH-].[Na+].C1COCC1>CO>[CH2:19]([N:15]1[C:16]2[C:11](=[C:10]([OH:36])[C:9]([C:7]([NH:6][CH2:5][CH2:4][C:3]([OH:37])=[O:2])=[O:8])=[N:18][CH:17]=2)[CH:12]=[C:13]([C:27]2[CH:32]=[N:31][C:30]([N:33]([CH3:35])[CH3:34])=[N:29][CH:28]=2)[C:14]1=[O:26])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 682975973-{[1-Benzyl-3-(2-dimethylamino-pyrimidin-5-yl)-5-hydroxy-2-oxo-1,2-dihydro-[1,7]naphthyridine-6-carbonyl]-amino}-propionic acid methyl ester

Product 1

HCID 601518213-{[1-Benzyl-3-(2-dimethylamino-pyrimidin-5-yl)-5-hydroxy-2-oxo-1,2-dihydro-[1,7]naphthyridine-6-carbonyl]-amino}-propionic acidYield 54.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-{[1-benzyl-3-(2-dimethylamino-pyrimidin-5-yl)-5-hydroxy-2-oxo-1,2-dihydro-[1,7]naphthyridine-6-carbonyl]-amino}-propionic acid methyl ester (30 mg, 0.060 mmol), 2 M NaOH (2 mL), THF (2 mL) and MeOH (2 mL) was stirred at r.t. overnight. The mixture was concentrated to approximately one-third of its original volume. 1 M HCl was added until pH was about 4, and the resulting suspension was extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated. The residue was dissolved in saturated NaHCO3 and washed several times with ether. The aqueous layer was acidified to pH about 4 with 6 M HCl, and the resulting precipitate was isolated by filtration to give 16 mg of the title compound as a pale yellow solid. MS: (+) m/z 489.29 (M+1).

Workup

  1. concentrationThe mixture was concentrated to approximately one-third of its original volume
  2. addition1 M HCl was added until pH was about 4
  3. extractionthe resulting suspension was extracted with EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in saturated NaHCO3
  7. washwashed several times with ether
  8. customthe resulting precipitate was isolated by filtration

Sources & evidence

ORD record
ord-9f469ac0610647d78928ddb387e5889e
Source dataset
uspto-grants-2014_12
Patent number
US08921389B2

Reaction notes

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