Methanol → 4-(4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2-oxo-2H-chromen-8-yloxy)butanoic acid

HRID 20666Notes

Reaction equation

HRID 20666 reaction equation
[OH-].[Li+].[Cl:3][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([Cl:33])[C:9]=1[NH:10][C:11]1[C:20]2[C:15](=[C:16]([O:23][CH2:24][CH2:25][CH2:26][C:27]([O:29]CC)=[O:28])[C:17]([O:21][CH3:22])=[CH:18][CH:19]=2)[O:14][C:13](=[O:32])[CH:12]=1.CO>C1COCC1>[Cl:3][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([Cl:33])[C:9]=1[NH:10][C:11]1[C:20]2[C:15](=[C:16]([O:23][CH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])[C:17]([O:21][CH3:22])=[CH:18][CH:19]=2)[O:14][C:13](=[O:32])[CH:12]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 24849622Ethyl 4-(4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2-oxo-2H-chromen-8-yloxy)butanoate

Product 1

HCID 248496684-(4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2-oxo-2H-chromen-8-yloxy)butanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (0.5 mL, IM, 0.5 mmol) was added to a solution of ethyl 4-(4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2-oxo-2H-chromen-8-yloxy)butanoate (12 mg, 0.026 mmol, Example 36), MeOH (0.5 mL), and THF (1.5 mL). The mixture was stirred 4 h, quenched with 1N HCl (20 mL), and extracted with EtOAc (30 mL×2). The organic extract was dried, filtered, and concentrated to give 4-(4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2-oxo-2H-chromen-8-yloxy)butanoic acid: 1H NMR (400 MHz, DMSO-d6): δ 9.52 (s, 1H), 8.81 (s, 2H), 7.94 (d, 1H), 7.20 (d, 1H), 4.64 (s, 1H), 4.00 (t, 2H), 3.91 (s, 3H), 2.46 (t, 2H), 1.88 (m, 2H); MS (ESI): 438.9.

Workup

  1. customquenched with 1N HCl (20 mL)
  2. extractionextracted with EtOAc (30 mL×2)
  3. extractionThe organic extract
  4. customwas dried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e9234c45853e4efca2e7d9b62d465cb4
Source dataset
uspto-grants-2010_06
Patent number
US07745646B2

Reaction notes

Loading…