Selectfluor → HCID 73504796, compound

HRID 590811Notes

Reaction equation

HRID 590811 reaction equation
[C:1]1([C@H:7]([NH:9][C:10](=[O:25])[NH:11][C:12]2[N:17]=[CH:16][C:15]3[C:18]([NH:21][C:22](=[O:24])[CH3:23])=[N:19][NH:20][C:14]=3[CH:13]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[B-](F)(F)(F)[F:27].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>CC(N(C)C)=O.CO>[F:27][C:13]1[C:14]2[NH:20][N:19]=[C:18]([NH:21][C:22](=[O:24])[CH3:23])[C:15]=2[CH:16]=[N:17][C:12]=1[NH:11][C:10]([NH:9][C@@H:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:8])=[O:25]

Participants

5

Reactant 2

HCID 2724933SelectfluorHCID 73504793HCID 73504793, compound

Product 1

HCID 73504796HCID 73504796, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 31374DimethylacetamideSolvent

Procedure

(R)—N-(6-(3-(1-Phenylethyl)ureido)-1H-pyrazolo[4,3-c]pyridin-3-yl)acetamide (Example 47; 75 mg, 0.222 mmol) was dissolved in DMA (0.5 mL) and methanol (0.5 mL), charged with powdered Selectfluor® (86 mg, 0.244 mmol), and stirred at room temperature overnight. The reaction was then heated to 65° C. for 2 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)—N-(7-fluoro-6-(3-(1-phenylethyl)ureido)-1H-pyrazolo[4,3-c]pyridin-3-yl)acetamide. MS ESI calc'd. for C17H17FN6O2 [M+1]+ 357. found 357. 1H NMR (500 MHz, DMSO-d6) δ 13.83 (s, 1H) 11.15 (s, 1H), 10.79 (s, 1H), 9.86 (s, 1H), 8.28 (d, J=7.3, 1H) 7.34 (m, 4H), 7.34 (m, 1H), 4.88 (m, 1H), 2.20 (S, 3H), 1.43 (d, J=6.9, 3H).

Workup

  1. temperatureThe reaction was then heated to 65° C. for 2 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-f4f3eb1f39cf4e7c8f4dd7408ee1c6a5
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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