Sodium Hydroxide → HCID 44816889, compound

HRID 1969438Notes

Reaction equation

HRID 1969438 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:31])[C:5]([C:26]([O:28]CC)=[O:27])=[CH:6][N:7]2[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH:23]=[CH:22][C:21]([CH2:24]O)=[N:20]2)=[CH:15][CH:14]=1.COCCN(S(F)(F)[F:42])CCOC.[OH-].[Na+]>O1CCCC1>[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:31])[C:5]([C:26]([OH:28])=[O:27])=[CH:6][N:7]2[CH2:12][C:13]1[CH:14]=[CH:15][C:16]([N:19]2[CH:23]=[CH:22][C:21]([CH2:24][F:42])=[N:20]2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 58297057HCID 58297057, compound

Product 1

HCID 44816889HCID 44816889, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 5-fluoro-1-{4-[3-(hydroxymethyl)-1H-pyrazol-1-yl]benzyl}-4-oxo-1,4-dihydroquinoline-3-carboxylate (0.050 g, 0.119 mmol) in 2 mL of tetrahydrofuran was cooled to −40° C. under nitrogen, and [bis(2-methoxyethyl)-amino]sulfur trifluoride (0.029 g, 0.13 mmol) was added. The reaction mixture was warmed to room temperature and after 4 hours 1 N NaOH (0.50 mL, 0.50 mmol) was added. After 30 minutes, the tetrahydrofuran was removed in vacuo, and 1 mL DMSO and 0.5 mL 40% NaOH were added. After 3 hours, the reaction mixture was acidified with 6 N HCl to pH ˜2, filtered, and purified via reverse phase HPLC to provide the title compound which gave a proton NMR spectrum consistent with theory and a mass ion (ES+) of 395.9 for M+H+: 1H NMR (400 MHz, d6-DMSO) δ 9.30 (s, 1H), 8.50 (s, 1H), 7.87-7.80 (m, 3H), 7.66 (d, J=8.8 Hz, 1H), 7.43 (d, J=8.6 Hz, 2H), 7.40-7.35 (m, 1H), 6.67 (s, 1H), 6.52 (s, 1H), 5.88 (s, 2H), 5.62 (d, J=10.2 Hz, 2H).

Workup

  1. additionwas added
  2. customthe tetrahydrofuran was removed in vacuo, and 1 mL DMSO and 0.5 mL 40% NaOH
  3. additionwere added
  4. waitAfter 3 hours
  5. filtrationfiltered
  6. custompurified via reverse phase HPLC

Sources & evidence

ORD record
ord-1090a0914feb4dd8ac4cfc4262fb462e
Source dataset
uspto-grants-2013_04
Patent number
US08426598B2

Reaction notes

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