L-Methionine → HCID 86721026, compound

HRID 524967Notes

Reaction equation

HRID 524967 reaction equation
[H-].[Na+].[NH2:3][C:4]1[C:13]([C:14]([NH:16][C:17]2[CH:22]=[N:21][CH:20]=[C:19]3[NH:23][CH:24]=[CH:25][C:18]=23)=[O:15])=[C:7]2[N:8]=[CH:9][C:10]([F:12])=[CH:11][N:6]2[N:5]=1.N[C@H:27](C(O)=O)CCSC>CN(C=O)C.O>[NH2:3][C:4]1[C:13]([C:14]([NH:16][C:17]2[CH:22]=[N:21][CH:20]=[C:19]3[N:23]([CH3:27])[CH:24]=[CH:25][C:18]=23)=[O:15])=[C:7]2[N:8]=[CH:9][C:10]([F:12])=[CH:11][N:6]2[N:5]=1

Participants

6

Reactant 3

HCID 6137L-MethionineHCID 24758Sodium hydrideHCID 86721027HCID 86721027, compound

Product 1

HCID 86721026HCID 86721026, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6228DimethylformamideSolvent

Procedure

NaH (3.958 mg, 0.09894 mmol) was added to a suspension of 2-amino-6-fluoro-N-(1H-pyrrolo[2,3-c]pyridin-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (28 mg, 0.08995 mmol) (synthesized according to a procedure similar to Example 1 or Example 3a) and Met (11.49 mg, 5.039 μL, 0.08096 mmol) in DMF (3 mL) under N2. The suspension was stirred at RT for 5 h before water (2 drops) was added. The crude mixture was purified by fractionlynx HPLC. Clean fractions were liophilized to yield 2-amino-6-fluoro-N-(1-methyl-1H-pyrrolo[2,3-c]pyridin-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (5 mg, 16%). MS (ES+) 326.1.

Workup

  1. customsynthesized
  2. additionwas added
  3. customThe crude mixture was purified by fractionlynx HPLC

Sources & evidence

ORD record
ord-96fef63563744a8a90c7ebdf6bb60d5b
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

Loading…