2-Methoxyethylamine → 1-(2-methoxy-ethyl)-2,6-dimethyl-4-(3-methyl-1H-indazol-5-yl)-1,4-dihydro-pyridine-3,5-dicarbonitrile

HRID 218501

반응식

HRID 218501 반응식
[NH2:1]/[C:2](/[CH3:6])=[CH:3]\[C:4]#[N:5].[CH3:7][O:8][CH2:9][CH2:10]N.[CH3:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([CH:22]=O)[CH:20]=2)[NH:15][N:14]=1>C(O)C>[CH3:7][O:8][CH2:9][CH2:10][N:1]1[C:2]([CH3:6])=[C:3]([C:4]#[N:5])[CH:22]([C:19]2[CH:20]=[C:21]3[C:16](=[CH:17][CH:18]=2)[NH:15][N:14]=[C:13]3[CH3:12])[C:3]([C:4]#[N:5])=[C:2]1[CH3:6]

참가 물질

5

반응물 3

HCID 80182-MethoxyethylamineHCID 5325263(2Z)-3-Amino-2-butenenitrileHCID 178434286HCID 178434286, 화합물

생성물 1

HCID 1784957891-(2-methoxy-ethyl)-2,6-dimethyl-4-(3-methyl-1H-indazol-5-yl)-1,4-dihydro-pyridine-3,5-dicarbonitrile수율 6.3%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
100 °C

실험 절차

164.2 mg (2 mmols) 3-aminocrotononitrile and 150.2 mg (2 mmols) 2-methoxyethylamine were dissolved in 8 mL ethanol and refluxed under argon for 3 hours. The solvent was distilled off under vacuum and the residue dissolved in 10 mL acetic acid. 160.2 mg (1 mmol) 3-methyl-1H-indazole-5-carbaldehyde (from Synthetic Preparation 10) were added. The mixture was stirred for 3 hours at 100° C. and then concentrated under vacuum. Purification by column chromatography gave 1-(2-methoxy-ethyl)-2,6-dimethyl-4-(3-methyl-1H-indazol-5-yl)-1,4-dihydro-pyridine-3,5-dicarbonitrile (22 mg) (Cpd. No. 310). 1H-NMR (DMSO-d6): δ=12.68 (br s, 1H), 7.51 (s, 1H), 7.47 (d, 1H), 7.26 (d, 1H), 4.40 (s, 1H), 3.86 (t, 2H), 3.52 (t, 2H), 3.37 (s, 3H), 2.50 (s, 3H; covered by DMSO), 2.25 (s, 6H) ppm.

후처리

  1. temperaturerefluxed under argon for 3 hours
  2. distillationThe solvent was distilled off under vacuum
  3. dissolutionthe residue dissolved in 10 mL acetic acid
  4. concentrationconcentrated under vacuum
  5. customPurification by column chromatography

출처 및 근거

ORD 기록
ord-a3db22863c6943cea65d2d4ba77c870e
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198456B2

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