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 476043

반응식

HRID 476043 반응식
[CH:1]1([C:4](=O)[CH2:5][C:6](=O)[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1.[CH3:14][C:15]([N:18]1[C:22]([NH2:23])=[CH:21][C:20]([CH3:24])=[N:19]1)([CH3:17])[CH3:16]>C1(C)C=CC=CC=1>[CH:1]1([C:4]2[CH:5]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:21]3[C:20]([CH3:24])=[N:19][N:18]([C:15]([CH3:17])([CH3:16])[CH3:14])[C:22]=3[N:23]=2)[CH2:3][CH2:2]1

참가 물질

4

반응물 2

HCID 7372001-tert-Butyl-3-methyl-1H-pyrazol-5-amineHCID 16779961Ethyl 4-cyclopropyl-2,4-dioxobutanoate

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

The title compound was prepared in the same manner as described for intermediate 33 using ethyl 4-cyclopropyl-2,4-dioxobutanoate (481 mg, 2.61 mmol), 1-(1,1-dimethylethyl)-3-methyl-1H-pyrazol-5-amine (400 mg, 2.61 mmol), and toluene (20 mL), wherein the reaction time was 3 h. The crude product was purified via silica gel chromatography (eluent: 0 to 10% EtOAc:Hex). The final product was collected as 0.24 g (30%). LCMS E-S (M+H)=302.5. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.02-1.23 (m, 4H) 1.47 (t, J=7.20 Hz, 3H) 1.79 (s, 9H) 2.19 (s, 1H) 2.66 (s, 3H) 4.49 (q, J=7.07 Hz, 2H) 7.44 (s, 1H).

후처리

  1. customThe crude product was purified via silica gel chromatography (eluent: 0 to 10% EtOAc:Hex)
  2. customThe final product was collected as 0.24 g (30%)

출처 및 근거

ORD 기록
ord-05f3cbc24f944193889ceca8d2f20d86
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637509B2

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