Pyridine → HCID 22987976, compound

HRID 986983Notes

Reaction equation

HRID 986983 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 s 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-03fc2b807cb548d19fe641755ccc7739
Source dataset
uspto-grants-2003_10
Patent number
US06630485B2

Reaction notes

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