1-(1-Cyclopropylethyl)-3-methyl-1H-pyrazol-5-amine → Ethyl 6-cyclopropyl-1-(1-cyclopropylethyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

HRID 476044Notes

Reaction equation

[CH:1]1([CH:4]([N:6]2[C:10]([NH2:11])=[CH:9][C:8]([CH3:12])=[N:7]2)[CH3:5])[CH2:3][CH2:2]1.[CH:13]1([C:16](=O)[CH2:17][C:18](=O)[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:15][CH2:14]1>C1(C)C=CC=CC=1>[CH:13]1([C:16]2[CH:17]=[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:9]3[C:8]([CH3:12])=[N:7][N:6]([CH:4]([CH:1]4[CH2:3][CH2:2]4)[CH3:5])[C:10]=3[N:11]=2)[CH2:14][CH2:15]1

Participants

Conditions

Temperature: 70 °C

Procedure

1-(1-Cyclopropylethyl)-3-methyl-1H-pyrazol-5-amine (500 mg, 3.03 mmol) and ethyl 4-cyclopropyl-2,4-dioxobutanoate (557 mg, 3.03 mmol) were suspended in Toluene (10 mL) and heated at 70° C. for 16 h. The solvent was removed in vacuo and the crude residue was purified via silica gel chromatography (eluent: gradient of 0 to 10% EtOAc:Hex). The final product was collected as a solid, 0.722 g (76%). LCMS E-S (M+H)=314.3 1H NMR (400 MHz, DMSO-d6) ppm 0.17-0.32 (m, 2H), 0.39 (m, J=9.69, 4.82, 4.82, 4.67 Hz, 1H), 0.51-0.62 (m, 1H), 0.94-1.11 (m, 4H), 1.28-1.41 (m, 4H), 1.58 (d, J=6.82 Hz, 3H), 2.30-2.38 (m, 1H), 2.56 (s, 3H), 4.19 (dq, J=9.44, 6.87 Hz, 1H), 4.43 (q, J=7.07 Hz, 2H), 7.48 (s, 1H)

Workup

customThe solvent was removed in vacuo
customthe crude residue was purified via silica gel chromatography (eluent: gradient of 0 to 10% EtOAc:Hex)
customThe final product was collected as a solid, 0.722 g (76%)

Sources & evidence

ORD record: ord-7834dd40e4f249febae8c38295eb285c
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637509B2

Reaction notes

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