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Methanol → {1-[(1-Benzyl-5-hydroxy-2-oxo-3-phenyl-8-pyridin-3-yl-1,2-dihydro-[1,7]naphthyridine-6-carbonyl)-amino]-cyclopropyl}-acetic acid

HRID 920107
Notes
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Reaction equation

HRID 920107 reaction equation
C[O:2][C:3](=[O:42])[CH2:4][C:5]1([NH:8][C:9]([C:11]2[C:12]([OH:41])=[C:13]3[C:18](=[C:19]([C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)[N:20]=2)[N:17]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:16](=[O:34])[C:15]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:14]3)=[O:10])[CH2:7][CH2:6]1.[OH-].[Na+].CO.C1COCC1>C([O-])(O)=O.[Na+]>[CH2:27]([N:17]1[C:18]2[C:13](=[C:12]([OH:41])[C:11]([C:9]([NH:8][C:5]3([CH2:4][C:3]([OH:42])=[O:2])[CH2:6][CH2:7]3)=[O:10])=[N:20][C:19]=2[C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[CH:14]=[C:15]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:16]1=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 68297247{1-[(1-Benzyl-5-hydroxy-2-oxo-3-phenyl-8-pyridin-3-yl-1,2-dihydro-[1,7]naphthyridine-6-carbonyl)-amino]-cyclopropyl}-acetic acid methyl ester

Product 1

HCID 68297192{1-[(1-Benzyl-5-hydroxy-2-oxo-3-phenyl-8-pyridin-3-yl-1,2-dihydro-[1,7]naphthyridine-6-carbonyl)-amino]-cyclopropyl}-acetic acid
Yield 47.3%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of {1-[(1-benzyl-5-hydroxy-2-oxo-3-phenyl-8-pyridin-3-yl-1,2-dihydro-[1,7]naphthyridine-6-carbonyl)-amino]-cyclopropyl}-acetic acid methyl ester (5 mg, 0.0089 mmol), 2 M NaOH (3 mL), MeOH (3 mL) and THF (3 mL) was stirred at r.t. for 2 days, then concentrated to approximately one-third of its original volume. 1 M HCl was added until pH was about 3, and the resulting suspension was extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated. The crude product was purified by silica gel chromatography (5-90% EtOAc/hexanes+1% AcOH). The product isolated was dissolved in saturated NaHCO3 and washed several times with ether. The aqueous layer was acidified to pH about 3, and the resulting suspension was extracted with CH2Cl2. The organic layer was dried over MgSO4 and concentrated to give 2.3 mg of the title compound as a yellow solid. MS: (+) m/z 547.35 (M+1).

Workup

  1. concentrationconcentrated to approximately one-third of its original volume
  2. addition1 M HCl was added until pH was about 3
  3. extractionthe resulting suspension was extracted with EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel chromatography (5-90% EtOAc/hexanes+1% AcOH)
  7. customThe product isolated
  8. washwashed several times with ether
  9. extractionthe resulting suspension was extracted with CH2Cl2
  10. dry with materialThe organic layer was dried over MgSO4
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-838452e5ec5b4bdb973ebaa1d634ec42
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09271970B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes