Hydrochloric Acid → 4-[(3,5-difluorobenzyl)amino]-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyridine-3-carboxyamide

HRID 2035544Notes

Reaction equation

HRID 2035544 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:36]=[C:37]([F:39])[CH:38]=1)[CH2:5][NH:6][C:7]1[CH:12]=[C:11]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[CH:19][CH:20]=3)[N:15](S(C3C=CC(C)=CC=3)(=O)=O)[CH:14]=2)[N:10]=[CH:9][C:8]=1[CH2:32][C:33]([NH2:35])=[O:34].Cl>CO.[OH-].[Na+].O>[F:39][C:37]1[CH:36]=[C:4]([CH:3]=[C:2]([F:1])[CH:38]=1)[CH2:5][NH:6][C:7]1[CH:12]=[C:11]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[CH:19][CH:20]=3)[NH:15][CH:14]=2)[N:10]=[CH:9][C:8]=1[CH2:32][C:33]([NH2:35])=[O:34]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 1317310074-[(3,5-difluorobenzyl)amino]-6-{1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyridine-3-carboxyamide2×

Product 1

HCID 1317310084-[(3,5-difluorobenzyl)amino]-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyridine-3-carboxyamideYield 41%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

10 mg of 4-[(3,5-difluorobenzyl)amino]-6-{1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyridine-3-carboxyamide (the compound of Example 370) was dissolved in 0.5 mL of methanol, to which 0.5 mL of 6 mol/L sodium hydroxide in water was added, and stirred at room temperature for 4 hours. Under ice cooling, hydrochloric acid was added to acidify (about pH 1) the reaction mixture, and washed with chloroform. The aqueous layer was basified (about pH 8) with saturated sodium bicarbonate in water, extracted with chloroform, the extract was washed with water, and dried on anhydrous sodium sulfate. The solvent was evaporated to obtain 2.9 mg (yield 41%) of the title compound as a white solid.

Workup

  1. additionwas added
  2. washwashed with chloroform
  3. extractionextracted with chloroform
  4. washthe extract was washed with water
  5. dry with materialdried on anhydrous sodium sulfate
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-3bd447680646492cab124c2533f966d8
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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