Methanol → 5-chloro-4-(8-(cyclopentyloxy)-7-methoxy-2-oxo-2H-chromen-4-ylamino)nicotinic acid

HRID 20651Notes

Reaction equation

HRID 20651 reaction equation
[OH-].[Li+].[Cl:3][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([C:13]=1[NH:14][C:15]1[C:24]2[C:19](=[C:20]([O:27][CH:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)[C:21]([O:25][CH3:26])=[CH:22][CH:23]=2)[O:18][C:17](=[O:33])[CH:16]=1)[C:9]([O:11]C)=[O:10].CO>C1COCC1>[Cl:3][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([C:13]=1[NH:14][C:15]1[C:24]2[C:19](=[C:20]([O:27][CH:28]3[CH2:29][CH2:30][CH2:31][CH2:32]3)[C:21]([O:25][CH3:26])=[CH:22][CH:23]=2)[O:18][C:17](=[O:33])[CH:16]=1)[C:9]([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 86618135methyl 5-chloro-4-(8-(cyclopentyloxy)-7-methoxy-2-oxo-2H-chromen-4-ylamino)nicotinate

Product 1

HCID 248495215-chloro-4-(8-(cyclopentyloxy)-7-methoxy-2-oxo-2H-chromen-4-ylamino)nicotinic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (1 mL, 1M, 1 mmol) was added to a solution of methyl 5-chloro-4-(8-(cyclopentyloxy)-7-methoxy-2-oxo-2H-chromen-4-ylamino)nicotinate, MeOH (0.8 mL), and THF (1.2 mL). The mixture was stirred for 3 h, quenched with 1N HCl (3 mL), and extracted with EtOAc. The organic extract was dried, filtered, concentrated and purified by reverse-phase HPLC (25→100% MeCN/H2O) to give 5-chloro-4-(8-(cyclopentyloxy)-7-methoxy-2-oxo-2H-chromen-4-ylamino)nicotinic acid: 1H NMR (400 MHz, DMSO-d6): δ 9.53 (s, 1H), 8.97 (s, 1H), 8.92 (s, 1H), 7.85 (d, 1H), 7.19 (d, 1H), 4.83 (m, 1H), 4.74 (s, 1H), 3.90 (s, 3H) 1.85-1.54 (m, 8H); MS (ESI): 430.9.

Workup

  1. customquenched with 1N HCl (3 mL)
  2. extractionextracted with EtOAc
  3. extractionThe organic extract
  4. customwas dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by reverse-phase HPLC (25→100% MeCN/H2O)

Sources & evidence

ORD record
ord-11dc56bf767a4908922ff195d6ff9076
Source dataset
uspto-grants-2010_06
Patent number
US07745646B2

Reaction notes

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