Water → HCID 178513703, compound

HRID 2196689Notes

Reaction equation

HRID 2196689 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[N:9][CH:10]=1)N[CH:6]=[CH:5]2.[F:11][C:12]1[C:20]([N+:21]([O-:23])=[O:22])=CC=[C:17]([F:24])[C:13]=1[C:14](O)=[O:15].C[CH2:26][N:27]=C=NCCCN(C)C.C1C=CC2N(O)N=[N:42]C=2C=1.O>CN(C=O)C.[Cl-].[Na+].O>[F:24][C:17]1[C:5]([C:4]2[CH:3]=[C:2]3[N:1]=[CH:26][NH:27][C:10]3=[N:9][CH:8]=2)=[CH:6][C:20]([N+:21]([O-:23])=[O:22])=[C:12]([F:11])[C:13]=1[C:14]([NH2:42])=[O:15]

Participants

8

Reactant 5

HCID 962WaterHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 3026292,6-Difluoro-3-nitrobenzoic acidHCID 117151871H-pyrrolo(2,3-b)pyridin-5-amine

Product 1

HCID 178513703HCID 178513703, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

5-Amino-7-azaindole (820 mg, 6.2 mmol), 2,6-difluoro-3-nitrobenzoic acid (1200 mg, 6.2 mmol), EDCI (1200 mg, 6.2 mmol), and HOBt.H2O (930 mg, 6.2 mmol) were combined in dry DMF (20 mL) and stirred at room temperature for 16 hours. The reaction mixture was then diluted with brine, extracted with EtOAc (2×), extracts washed with water (1×), dried over sodium sulfate and concentrated under reduced pressure. The resulting crude product was purified via silica gel chromatography using an ISCO system (5% MeOH/DCM) to provide 2,6-difluoro-5-nitro-(3H-imidazo[4,5-b]pyridin-6-yl)benzamide (1.76 g, 88%). m/z (LC-MS) M+1=319.

Workup

  1. extractionextracted with EtOAc (2×)
  2. washextracts washed with water (1×)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting crude product was purified via silica gel chromatography

Sources & evidence

ORD record
ord-a8ea201955984a27b0045bba99264836
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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