tert-Butyl N-(2-bromoethyl)carbamate → Ethyl 6-cyclopropyl-1-[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

HRID 476048노트

반응식

HRID 476048 반응식
[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+].Br[CH2:25][CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31]>CN(C=O)C>[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][N:10]([CH2:25][CH2:26][NH:27][C:28]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:34])[C:8]=3[N:9]=2)[CH2:2][CH2:3]1

참가 물질

5

반응물 3

HCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 23665647Potassium tert-butoxideHCID 67124108ethyl 6-cyclopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

생성물 1

HCID 68078825Ethyl 6-cyclopropyl-1-[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Ethyl 6-cyclopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (125 mg, 0.541 mmol) was dissolved in DMF (10 mL), followed by addition of potassium tert-butoxide (79 mg, 0.703 mmol). After stirring for 15 minutes, 1,1-dimethylethyl (2-bromoethyl)carbamate (121 mg, 0.541 mmol) was added and the mixture was stirred at room temperature for 16 h. The reaction mixture was concentrated to dryness. The crude residue was diluted with water (50 mL) and acidified with acetic acid. The contents were extracted with DCM (4×50 mL). The combined organic layers were washed with water, brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was purified via silica gel chromatography (eluent: 0 to 50% EtOAc:Hex). The final product was obtained as 0.114 g (56%). LCMS E-S (M+H)=375.1. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.04-1.14 (m, 4H), 1.15-1.20 (m, 2H), 1.27 (s, 7H), 1.41 (t, J=7.07 Hz, 3H), 2.36-2.45 (m, 1H), 3.31-3.41 (m, 3H), 4.36-4.50 (m, 5H), 6.84 (t, J=5.81 Hz, 1H), 7.65 (s, 1H), 8.24 (s, 3H).

후처리

  1. stirringthe mixture was stirred at room temperature for 16 h
  2. concentrationThe reaction mixture was concentrated to dryness
  3. additionThe crude residue was diluted with water (50 mL)
  4. extractionThe contents were extracted with DCM (4×50 mL)
  5. washThe combined organic layers were washed with water, brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was purified via silica gel chromatography (eluent: 0 to 50% EtOAc:Hex)

출처 및 근거

ORD 기록
ord-c1eaebf221f54d7fa5e3b1d05e1f43ae
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637509B2

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