HCID 71253722, compound → HCID 71254180, compound

HRID 1775037Notes

Reaction equation

HRID 1775037 reaction equation
[C:1]1([C:6]2[C:14]3[C:9](=[CH:10][N:11]=[C:12]([C:15]4[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=4)[CH:13]=3)[N:8](C3CCCCO3)[N:7]=2)[CH2:5][CH2:4][CH2:3][CH:2]=1>FC(F)(F)C(O)=O>[C:1]1([C:6]2[C:14]3[C:9](=[CH:10][N:11]=[C:12]([C:15]4[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=4)[CH:13]=3)[NH:8][N:7]=2)[CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

3

Reactant 1

HCID 71253722HCID 71253722, compound

Product 1

HCID 71254180HCID 71254180, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 35 mg (0.10 mmol) of 3-cyclopentenyl-5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine in 4 ml of trifluoroacetic acid was stirred for 6 hours. The mixture was concentrated in vacuum, the residue partitioned between saturated aqueous solution of NaHCO3 and ethyl acetate. The organic extracts were washed with water, brine, dried over MgSO4 and concentrated. The residue was purified via reverse phase HPLC using a gradient of MeOH in water with 0.1% NH4OH to afford 10 mg (38%) of 225. ESI MS m/z 263.0 (M+1). 1H NMR (400 MHz, DMSO): 13.59 (s, 1H), 9.39 (s, 1H), 9.14 (s, 1H), 8.53-8.600 (m, 3H), 7.50 (dd, J=7.9, 4.8 Hz, 1H), 6.88 (s, 1H), 2.91 (t, J=6.6 Hz, 2H), 2.64 (s, 2H), 2.04-1.94 (m, 2H)

Workup

  1. concentrationThe mixture was concentrated in vacuum
  2. customthe residue partitioned between saturated aqueous solution of NaHCO3 and ethyl acetate
  3. washThe organic extracts were washed with water, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified via reverse phase HPLC

Sources & evidence

ORD record
ord-94e2c2ce22b0494db9ce331d410e4604
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

Loading…