Trimethylaluminum → HCID 178489754, 화합물

HRID 1911370노트

반응식

HRID 1911370 반응식
[CH:1]1([N:4]2[CH2:9][CH2:8][CH:7]([C:10]3[CH:19]=[CH:18][C:13]([C:14]([O:16]C)=O)=[CH:12][CH:11]=3)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH2:30][CH2:31][C:32]2[CH:33]=[C:34]([NH2:37])[NH:35][N:36]=2)[CH:25]=[C:26]([O:28][CH3:29])[CH:27]=1.C[Al](C)C>C1(C)C=CC=CC=1>[CH:1]1([N:4]2[CH2:5][CH2:6][CH:7]([C:10]3[CH:11]=[CH:12][C:13]([C:14]([NH:37][C:34]4[NH:35][N:36]=[C:32]([CH2:31][CH2:30][C:24]5[CH:25]=[C:26]([O:28][CH3:29])[CH:27]=[C:22]([O:21][CH3:20])[CH:23]=5)[CH:33]=4)=[O:16])=[CH:18][CH:19]=3)[CH2:8][CH2:9]2)[CH2:2][CH2:3]1

참가 물질

5

반응물 3

HCID 16682925TrimethylaluminumHCID 57440413Methyl 4-(1-cyclopropylpiperidin-4-yl)benzoateHCID 178489815HCID 178489815, 화합물

생성물 1

HCID 178489754HCID 178489754, 화합물수율 35.8%

시약·촉매·용매 1

HCID 1140Toluene용매2회

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온도
60 °C

실험 절차

Methyl 4-(1-cyclopropylpiperidin-4-yl)benzoate (0.259 g, 1 mmol), 5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-amine (0.247 g, 1.00 mmol) in toluene (10 ml) was treated with a 2M solution of trimethylaluminium (1.250 ml, 2.50 mmol) in toluene, under nitrogen. The reaction mixture was heated at 60° C. for 18 h. The reaction mixture was cooled and the reaction quenched with methanol (40 ml) and acidified with 2N HCl (1 ml). The crude reaction mixture was purified by ion exchange chromatography, using an SCX column. The crude product was eluted from the column using 7M NH3/MeOH and fractions were evaporated to dryness. The crude product was purified by silica column chromatography, eluting with a gradient of 0 to 5% 2.5M ammonia/methanol in DCM. Pure fractions were evaporated to dryness and the product crystallised from DCM/diethyl ether to give the title compound (0.170 g, 35.8%) as a white solid.

후처리

  1. temperatureThe reaction mixture was cooled
  2. customthe reaction quenched with methanol (40 ml)
  3. customThe crude reaction mixture
  4. customwas purified by ion exchange chromatography
  5. washThe crude product was eluted from the column
  6. customwere evaporated to dryness
  7. customThe crude product was purified by silica column chromatography
  8. washeluting with a gradient of 0 to 5% 2.5M ammonia/methanol in DCM
  9. customPure fractions were evaporated to dryness
  10. customthe product crystallised from DCM/diethyl ether

출처 및 근거

ORD 기록
ord-2e39100966374d94a1ecdc67be75a14f
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08604022B2

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