3-(6-Fluoropyridin-2-yl)-5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine → 3-(6-fluoropyridin-2-yl)-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine

HRID 1774971Notes

Reaction equation

HRID 1774971 reaction equation
[F:1][C:2]1[N:7]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][N:13]=[C:14]([C:17]4[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=4)[CH:15]=3)[N:10](C3CCCCO3)[N:9]=2)[CH:5]=[CH:4][CH:3]=1>CO.Cl.O1CCOCC1>[F:1][C:2]1[N:7]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][N:13]=[C:14]([C:17]4[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=4)[CH:15]=3)[NH:10][N:9]=2)[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 712536623-(6-Fluoropyridin-2-yl)-5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine

Product 1

HCID 712537483-(6-fluoropyridin-2-yl)-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridineYield 101.9%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 120 mg (0.32 mmol) of 3-(6-fluoropyridin-2-yl)-5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine from Example 10 in 3 ml of methanol, 12 ml of 4N HCl in dioxane was added. The mixture was stirred for 8 hours and concentrated in vacuum. The residue was triturated with ethyl ether. The solid material was filtered out, washed with ethyl ether and dried. The above solid was dispersed in 30 ml of saturated aqueous sodium bicarbonate and the suspension was stirred for 1 hour. The solid base was collected, washed with water and dried in high vacuum for 24 hours to yield 95 mg of 131 (90%). ESI MS m/z 292.1 (M+1). 1H NMR (400 MHz, DMSO): 9.32-9.21 (m, 1H), 8.81 (s, 1H), 8.61 (dd, J=4.7, 1.4 Hz, 1H), 8.42 (d, J=8.0 Hz, 1H), 8.21-8.06 (m, 1H), 7.55 (dd, J=7.9, 4.7 Hz, 1H), 7.18 (d, J=7.7 Hz, 1H), 6.53 (s, 1H), 6.28 (s, 1H)

Workup

  1. additionwas added
  2. concentrationconcentrated in vacuum
  3. customThe residue was triturated with ethyl ether
  4. filtrationThe solid material was filtered out
  5. washwashed with ethyl ether
  6. customdried
  7. additionThe above solid was dispersed in 30 ml of saturated aqueous sodium bicarbonate
  8. stirringthe suspension was stirred for 1 hour
  9. customThe solid base was collected
  10. washwashed with water
  11. customdried in high vacuum for 24 hours

Sources & evidence

ORD record
ord-c8bcfa49279f48caa140d79045c75541
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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