Hydrochloric Acid → HCID 22176530, compound

HRID 1797215Notes

Reaction equation

HRID 1797215 reaction equation
[F:1][C:2]([C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]([C:21]2[N:26]=[CH:25][C:24]([C:27]([O:29]C)=[O:28])=[CH:23][CH:22]=2)=[O:20])=[CH:14][CH:13]=1)([CH3:11])[CH2:3][NH:4][S:5]([CH:8]([CH3:10])[CH3:9])(=[O:7])=[O:6].[OH-].[Li+].O1CCCC1.Cl>O.CO>[F:1][C:2]([C:12]1[CH:13]=[CH:14][C:15]([NH:18][C:19]([C:21]2[N:26]=[CH:25][C:24]([C:27]([OH:29])=[O:28])=[CH:23][CH:22]=2)=[O:20])=[CH:16][CH:17]=1)([CH3:11])[CH2:3][NH:4][S:5]([CH:8]([CH3:10])[CH3:9])(=[O:6])=[O:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 22176524HCID 22176524, compound

Product 1

HCID 22176530HCID 22176530, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl 6-{N-[4-(1-fluoro-1-methyl-2-{[(methylethyl)sulfonyl]amino}ethyl)phenyl]carbamoyl}pyridine-3-carboxylate (150 mg, 0.35 mmol, prepared in example 50), lithium hydroxide (52 mg, 1.24 mmol), tetrahydrofuran (6 mL), methanol (2 mL), and water (2 mL) were mixed together in a 25 mL 3 neck flask and stirred over night at room temperature. In the morning, the mixture was concentrated under reduced vacuum to yield a white solid. This material was taken into 1N HCl and the desired material was extracted into methylene chloride. The acidic solution was taken to pH 10 with 1N NaOH and the resulting precipitate was again extracted with methylene chloride. Both organic layers were combined and washed once with H2O, dried over MgSO4, filtered, and concentrated under reduced vacuum to yield the title compound (125 mg, 84%) as a tan solid. This material was used without further purification. Ion spray M.S. 403.9 (M*−19 Fluorine).

Workup

  1. concentrationIn the morning, the mixture was concentrated under reduced vacuum
  2. customto yield a white solid
  3. extractionthe desired material was extracted into methylene chloride
  4. extractionthe resulting precipitate was again extracted with methylene chloride
  5. washwashed once with H2O
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced vacuum

Sources & evidence

ORD record
ord-406aa7edd5924905b656d36b1cb035a9
Source dataset
uspto-grants-2006_04
Patent number
US07034045B1

Reaction notes

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