Pyridine → HCID 22987976, compound

HRID 429211Notes

Reaction equation

HRID 429211 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:8][C:9]1[CH:14]=[C:13]([C:15]2[NH:23][C:18]3=[N:19][CH:20]=[CH:21][N:22]=[C:17]3[C:16]=2[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[CH:12]=[CH:11][N:10]=1.N1C=CC=CC=1.[C:37](Cl)(=[O:39])[CH3:38]>O1CCCC1.CO>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:37]([NH:8][C:9]1[CH:14]=[C:13]([C:15]2[NH:23][C:18]3=[N:19][CH:20]=[CH:21][N:22]=[C:17]3[C:16]=2[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[CH:12]=[CH:11][N:10]=1)(=[O:39])[CH3:38]

Participants

6

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 22987993HCID 22987993, compound

Product 1

HCID 22987976HCID 22987976, compoundYield 77.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

6-(2-Aminopyridin-4-yl)-7-(4-fluorophenyl)-5H-pyrrolo[2,3-b]pyrazine trifluoroacetate salt (0.085 g, 0.28 mmol) was dissolved in tetrahydrofuran and pyridine (0.22 g, 2.8 mmol) was added. Acetyl chloride (0.033 g, 0.42 mmol) in tetrahydrofuran (1 ml) was added and the resulting mixture was stirred at room temperature. After 1 h, the reaction mixture was diluted with methanol (2 ml) and the product was isolated by reverse phase HPLC to give 6-(2-acetylaminopyridin-4-yl)-7-(4-fluorophenyl)-5H-pyrrolo[2,3-b]pyrazine trifluoroacetate salt (0.1 g) as a yellow solid. The product was converted to the hydrochloride salt by suspending the product in ether and adding 1.0M solution of HCl in ether (2 ml) to give a solid which was filtered off to give 6-(2-acetylaminopyridin-4-yl)-7-(4-fluorophenyl)-5H-pyrrolo[2,3-b]pyrazine hydrochloride salt (0.0.44 g) as a yellow solid.

Workup

  1. customthe product was isolated by reverse phase HPLC

Sources & evidence

ORD record
ord-f100f95751e34d6291c66c5ee49d9525
Source dataset
uspto-grants-2001_11
Patent number
US06316464B1

Reaction notes

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