Trifluoroacetic acid → HCID 86767714, compound

HRID 523009Notes

Reaction equation

HRID 523009 reaction equation
[CH3:1][N:2]1[CH:17]=[C:5]2[N:6](C(OC(C)(C)C)=O)[CH2:7][CH2:8][CH2:9][C:4]2=[N:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][N:2]1[CH:17]=[C:5]2[NH:6][CH2:7][CH2:8][CH2:9][C:4]2=[N:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90041132HCID 90041132, compound

Product 1

HCID 86767714HCID 86767714, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 2-methyl-6,7-dihydro-2H-pyrazolo[4,3-b]pyridine-4(5H)-carboxylate (56 mg, 236 mol) in CH2Cl2 (4.00 mL) was added TFA (740 mg, 500 μL, 6.49 mmol) at room temperature. After 18 h, the reaction mixture was concentrated in vacuo and the residue obtained was purified by chromatography (40 g column, 50 m silica-gel from Analogix, 0 to 5% 9:1 methanol:ammonium hydroxide in CH2Cl2, 20 min) to give 2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-b]pyridine (25 mg, 77%). 1H NMR (CHLOROFORM-d) δ: 6.81 (s, 1H), 3.75 (s, 3H), 3.11-3.18 (m, 2H), 3.04 (s, 1H), 2.73 (t, J=6.4 Hz, 2H), 1.86-2.00 (m, 2H).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customthe residue obtained
  3. customwas purified by chromatography (40 g column, 50 m silica-gel from Analogix, 0 to 5% 9:1 methanol:ammonium hydroxide in CH2Cl2, 20 min)

Sources & evidence

ORD record
ord-431ccb6d54e0490fb5ca8c154ef84e1b
Source dataset
uspto-grants-2016_05
Patent number
US09334278B2

Reaction notes

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