Hydrochloric Acid → HCID 23000557, compound

HRID 397530Notes

Reaction equation

HRID 397530 reaction equation
C([O:3][C:4](=[O:26])[CH2:5][C:6]1[C:11]([Cl:12])=[CH:10][N:9]=[C:8]([NH:13][CH2:14][C:15]([F:24])([F:23])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N+:17]=2[O-:22])[C:7]=1[F:25])C.[Li+].[OH-].Cl>CO>[Cl:12][C:11]1[C:6]([CH2:5][C:4]([OH:26])=[O:3])=[C:7]([F:25])[C:8]([NH:13][CH2:14][C:15]([F:23])([F:24])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N+:17]=2[O-:22])=[N:9][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium Hydroxide2×HCID 59085845HCID 59085845, compound

Product 1

HCID 23000557HCID 23000557, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.58 g (1.49 mmol) ethyl(5-chloro-2-{[2,2-difluoro-2-(1-oxido-2-pyridinyl)ethyl]amino}-3-fluoro-4-pyridinyl)acetate 1-8 in 10 mL MeOH was added 1.64 mL (1.64 mmol, 1M aqueous solution) LiOH and the reaction mixture allowed to stir 16 hours at room temperature, then 0.16 mL (0.16 mmol) more LiOH was added and the mixture heated to 45° C. for 4 h, then cooled. To this was added 0.15 mL (1.79 mmol, 12M solution) HCl and the mixture concentrated to give (5-chloro-2-{[2,2-difluoro-2-(1-oxido-2-pyridinyl)ethyl]amino}-3-fluoro-4-pyridinyl)acetic acid 1-9 (mixed with LiCl). 1H NMR (400 mHz, CD3OD) δ8.36 (br d, 1H, J=6.23 Hz); 7.66 (dd, 1H, J=7.87 and 2.19 Hz); 7.56 (s, 1H); 7.51 (m, 2H,); 4.58 (t, 2H, J=13 Hz); 3.63 (d, 2H, J=1.65 Hz);

Workup

  1. temperaturethe mixture heated to 45° C. for 4 h
  2. temperaturecooled
  3. concentrationthe mixture concentrated

Sources & evidence

ORD record
ord-a5c51eded89f473f91f24b59ce99982c
Source dataset
uspto-grants-2003_08
Patent number
US06610701B2

Reaction notes

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