Sodium Hydroxide → HCID 57567285, compound

HRID 401426Notes

Reaction equation

HRID 401426 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][C:14]=1[NH:15][C:16]([C:18]1[C:27](=[O:28])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][CH:19]=1)=[O:17])[NH:11][CH:10]=[CH:9]2)=[O:5])C.[OH-].[Na+]>C1COCC1>[O:28]=[C:27]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[NH:20][CH:19]=[C:18]1[C:16]([NH:15][C:14]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][NH:11]2)=[CH:7][C:6]=1[C:4]([OH:5])=[O:3])=[O:17]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 575673926-[(4-oxo-1H-quinolin-3-yl)carbonylamino]-1H-indole-5-carboxylic acid ethyl ester

Product 1

HCID 57567285HCID 57567285, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 6-[(4-oxo-1H-quinolin-3-yl)carbonylamino]-1H-indole-5-carboxylic acid ethyl ester (188) (450 mg, 1.2 mmol) and 1N NaOH solution (5 mL) in THF (10 mL) was heated at 85° C. overnight. The reaction mixture was partitioned between EtOAc and water. The aqueous layer was acidified with 1N HCl solution to pH 5, and the precipitate was filtered, washed with water and air dried to yield 6-[(4-oxo-1H-quinolin-3-yl)carbonylamino]-1H-indole-5-carboxylic acid (188-I) (386 mg, 93%). 1H-NMR (400 MHz, DMSO-d6) δ 12.92-12.75 (m, 2H), 11.33 (s, 1H), 8.84 (s, 1H), 8.71 (s, 1H), 8.30 (dd, J=8.1, 0.9 Hz, 1H), 8.22 (s, 1H), 7.80-7.72 (m, 2H), 7.49 (t, J=8.0 Hz, 1H), 7.41 (t, J=2.7 Hz, 1H), 6.51 (m, 1H); HPLC ret. time 2.95 min, 10-99% CH3CN, 5 min run; ESI-MS 376.2 m/z (MH+).

Workup

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. filtrationthe precipitate was filtered
  3. washwashed with water and air
  4. customdried

Sources & evidence

ORD record
ord-0842ca686e004631845dfed380d1ef01
Source dataset
uspto-grants-2014_06
Patent number
US08741925B2

Reaction notes

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