1-tert-Butyl-3-methyl-1H-pyrazol-5-amine → ethyl 6-cyclopropyl-1-(1,1-dimethylethyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

HRID 1522525Notes

Reaction equation

HRID 1522525 reaction equation
[CH3:1][C:2]([N:5]1[C:9]([NH2:10])=[CH:8][C:7]([CH3:11])=[N:6]1)([CH3:4])[CH3:3].[CH:12]1(/[C:15](/O)=[CH:16]/[C:17](=O)[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH2:13]1>C(O)(=O)C>[CH:12]1([C:15]2[CH:16]=[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:8]3[C:7]([CH3:11])=[N:6][N:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[C:9]=3[N:10]=2)[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 7372001-tert-Butyl-3-methyl-1H-pyrazol-5-amineHCID 178473076HCID 178473076, compound

Product 1

HCID 68078897ethyl 6-cyclopropyl-1-(1,1-dimethylethyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1-(1,1-dimethylethyl)-3-methyl-1H-pyrazol-5-amine (166 mg, 1.086 mmol), ethyl (3Z)-4-cyclopropyl-4-hydroxy-2-oxo-3-butenoate (200 mg, 1.086 mmol) and acetic acid (10 mL) were heated to reflux for 2 hours. The solvent was removed in vacuo and the residue purified by silica gel chromatography (eluent: 0% to 7% EtOAc:Hex). The product was collected as 278 mg. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.07 (dt, 2 H), 1.13-1.20 (m, 2 H), 1.46 (t, J=7.20 Hz, 3 H), 1.78 (s, 9 H), 2.18 (m, J=7.99, 7.99, 4.74, 4.55 Hz, 1 H), 2.65 (s, 3 H), 4.47 (q, J=7.07 Hz, 2 H), 7.43 (s, 1 H). LCMS(ES) [M+H]+ 302.2

Workup

  1. temperatureto reflux for 2 hours
  2. customThe solvent was removed in vacuo
  3. customthe residue purified by silica gel chromatography (eluent: 0% to 7% EtOAc:Hex)
  4. customThe product was collected as 278 mg

Sources & evidence

ORD record
ord-d3910beb9ef6469f9d923362f55144bc
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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