Water → HCID 58412258, compound

HRID 40726Notes

Reaction equation

HRID 40726 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[C:9]([C:11]([OH:13])=O)[CH:10]=[C:5]2[CH:4]=[CH:3]1.[F:14][C:15]1[C:20]([NH2:21])=[CH:19][CH:18]=[C:17]([F:22])[N:16]=1.O>C(Cl)Cl.N1C=CC=CC=1>[F:14][C:15]1[C:20]([NH:21][C:11]([C:9]2[CH:10]=[C:5]3[CH:4]=[CH:3][N:2]([CH3:1])[C:6]3=[N:7][CH:8]=2)=[O:13])=[CH:19][CH:18]=[C:17]([F:22])[N:16]=1

Participants

6

Reactant 3

HCID 962WaterHCID 450800062,6-Difluoropyridin-3-amineHCID 497590021-Methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid

Product 1

HCID 58412258HCID 58412258, compoundYield 72.5%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (3.54 g, 20.1 mmol) in CH2Cl2 (400 mL) was added 1-chloro-N,N-2-trimethylpropenylamine (5.26 mL, 40.2 mmol). Following formation of the resulting acid chloride, the reaction mixture was concentrated affording a residue that was dissolved in pyridine (100 mL) before 2,6-difluoro-pyridin-3-ylamine (2.61 mg, 20.1 mmol) was added in one portion. After an additional 30 minutes the reaction mixture was concentrated to dryness affording a residue, to which was added water causing precipitation of analytically pure 1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (2,6-difluoro-pyridin-3-yl)-amide (4.2 g, 72.5% yield). ES MS (M+H+)=289.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customaffording a residue that
  3. additionwas added in one portion
  4. concentrationAfter an additional 30 minutes the reaction mixture was concentrated to dryness
  5. customaffording a residue
  6. additionto which was added

Sources & evidence

ORD record
ord-9856f9f1b13d40a291c55ed53f52a81d
Source dataset
uspto-grants-2013_09
Patent number
US08530483B2

Reaction notes

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