Potassium tert-butoxide → Ethyl 1-amino-6-cyclopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

HRID 1522431Notes

Reaction equation

HRID 1522431 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:7]3[CH:12]=[N:11][NH:10][C:8]=3[N:9]=2)[CH2:3][CH2:2]1.CC(C)([O-])C.[K+].[NH2:24]OC(C1C=CC(OC)=CC=1)=O.COC1C=CC(C(ON)=O)=CC=1>CN1CCCC1=O.CCOC(C)=O>[NH2:24][N:10]1[C:8]2[N:9]=[C:4]([CH:1]3[CH2:2][CH2:3]3)[CH:5]=[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:7]=2[CH:12]=[N:11]1

Participants

6

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 67124108ethyl 6-cyclopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylateHCID 117700466O-{[4-(methyloxy)phenyl]carbonyl}hydroxylamine 1-[(aminooxy)carbonyl]-4-(methyloxy)benzene

Product 1

HCID 67124432Ethyl 1-amino-6-cyclopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Ethyl 6-cyclopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (200 mg, 0.865 mmol) was dissolved in N-Methyl-2-pyrrolidone (NMP) (8 mL), followed by addition of potassium tert-butoxide (116 mg, 1.038 mmol). After 20 minutes stirring, O-{[4-(methyloxy)phenyl]carbonyl}hydroxylamine 1-[(aminooxy)carbonyl]-4-(methyloxy)benzene (289 mg, 1.730 mmol) was added and the mixture stirred at room temperature for 16 h. The contents were diluted with EtOAc, and then washed with brine, and saturated NaHCO3. The organic phase was dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified via silica gel chromatography (eluent: 0 to 50% EtOAc). The final product as collected as 106 mg (50%). LCMS E-S (M+H)=274.4. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.00-1.14 (m, 4 H), 1.41 (t, J=7.07 Hz, 3 H), 2.34-2.47 (m, 1 H), 4.44 (q, J=7.07 Hz, 2 H), 6.39 (s, 2 H), 7.64 (s, 1 H), 8.09 (s, 1 H).

Workup

  1. stirringthe mixture stirred at room temperature for 16 h
  2. washwashed with brine, and saturated NaHCO3
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified via silica gel chromatography (eluent: 0 to 50% EtOAc)
  7. customThe final product as collected as 106 mg (50%)

Sources & evidence

ORD record
ord-85689f9ec1394381bd58a4298c5d7770
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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