Selectfluor → (R)-1-(3-(ethylamino)-7-fluoro-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea

HRID 590809Notes

Reaction equation

HRID 590809 reaction equation
[CH2:1]([N:3]([C:7]1[C:11]2[CH:12]=[N:13][C:14]([NH:16][C:17]([NH:19][C@@H:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH3:21])=[O:18])=[CH:15][C:10]=2[NH:9][N:8]=1)C(=O)C)[CH3:2].[B-](F)(F)(F)[F:29].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>CC(N(C)C)=O.CO>[CH2:1]([NH:3][C:7]1[C:11]2[CH:12]=[N:13][C:14]([NH:16][C:17]([NH:19][C@@H:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH3:21])=[O:18])=[C:15]([F:29])[C:10]=2[NH:9][N:8]=1)[CH3:2]

Participants

5

Reactant 2

HCID 2724933SelectfluorHCID 118272482(R)-N-ethyl-N-(6-(3-(1-phenylethyl)ureido)-1H-pyrazolo[4,3-c]pyridin-3-yl)acetamide

Product 1

HCID 73504795(R)-1-(3-(ethylamino)-7-fluoro-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 31374DimethylacetamideSolvent

Procedure

(R)—N-Ethyl-N-(6-(3-(1-phenylethyl)ureido)-1H-pyrazolo[4,3-c]pyridin-3-yl)acetamide (154 mg, 0.420 mmol) was dissolved in DMA (1 mL) and methanol (1 mL), charged with powdered Selectfluor® (164 mg, 0.462 mmol), and stirred at room temperature overnight. The reaction was then to heated to 55° C. for 8 h. The resulting crude residue was purified by mass-triggered reverse phase HPLC. Fractions containing pure compound were filtered through a PS-HCO3 cartridge and the filtrate was concentrated in vacuo to give (R)-1-(3-(ethylamino)-7-fluoro-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea. MS ESI calc'd. for C19H21FN6O2 [M+1]+ 385. found 385.

Workup

  1. temperatureto heated to 55° C. for 8 h
  2. customThe resulting crude residue was purified by mass-triggered reverse phase HPLC
  3. additionFractions containing pure compound
  4. filtrationwere filtered through a PS-HCO3 cartridge
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-f23e1211075e4d55b7bc15b8e91056bf
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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