Triethylamine → 2-amino-6-fluoro-N-(5-fluoro-4-(4-((tetrahydro-2H-pyran-4-yl)sulfonyl)piperazin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 524931Notes

Reaction equation

HRID 524931 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([S:7](Cl)(=[O:9])=[O:8])[CH2:3][CH2:2]1.[NH2:11][C:12]1[C:21]([C:22]([NH:24][C:25]2[CH:26]=[N:27][CH:28]=[C:29]([F:37])[C:30]=2[N:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[O:23])=[C:15]2[N:16]=[CH:17][C:18]([F:20])=[CH:19][N:14]2[N:13]=1.CCN(CC)CC>CN(C=O)C>[NH2:11][C:12]1[C:21]([C:22]([NH:24][C:25]2[CH:26]=[N:27][CH:28]=[C:29]([F:37])[C:30]=2[N:31]2[CH2:36][CH2:35][N:34]([S:7]([CH:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)(=[O:9])=[O:8])[CH2:33][CH2:32]2)=[O:23])=[C:15]2[N:16]=[CH:17][C:18]([F:20])=[CH:19][N:14]2[N:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 22637030Oxane-4-sulfonyl chlorideHCID 867209892-amino-6-fluoro-N-(5-fluoro-4-piperazin-1-yl-3-pyridyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

Product 1

HCID 867209882-amino-6-fluoro-N-(5-fluoro-4-(4-((tetrahydro-2H-pyran-4-yl)sulfonyl)piperazin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Tetrahydropyran-4-sulfonyl chloride (16.28 mg, 0.08815 mmol) was added to a suspension of 2-amino-6-fluoro-N-(5-fluoro-4-piperazin-1-yl-3-pyridyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (30 mg, 0.08014 mmol) (synthesized according to the procedure similar to Example 2) and Et3N (12.16 mg, 16.75 μL, 0.1202 mmol) in DMF (0.2 mL). The crude mixture was purified by Fractionlynx HPLC. The clean aqueous fractions were combined and lyophilised, yielding 2-amino-6-fluoro-N-(5-fluoro-4-(4-((tetrahydro-2H-pyran-4-yl)sulfonyl)piperazin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide. MS (ES+) 523.1.

Workup

  1. customsynthesized
  2. customThe crude mixture was purified by Fractionlynx HPLC

Sources & evidence

ORD record
ord-d8aeed86df614bb0861c85afc113320d
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

Loading…