1,2-Dichloroethane → 5-[3-(4-Fluorophenyl)propanoyl]-4-(4-isopropylphenyl)-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine

HRID 1071995

반응식

HRID 1071995 반응식
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[C:15]3[N:16]=[CH:17][NH:18][C:14]=3[CH2:13][CH2:12][NH:11]2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[F:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28](O)=[O:29])=[CH:22][CH:21]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>C(Cl)Cl>[F:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:26][CH2:27][C:28]([N:11]2[CH2:12][CH2:13][C:14]3[NH:18][CH:17]=[N:16][C:15]=3[CH:10]2[C:7]2[CH:8]=[CH:9][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=2)=[O:29])=[CH:24][CH:25]=1

참가 물질

6

반응물 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 1363023-(4-Fluorophenyl)propionic acidHCID 31167414-(4-isopropylphenyl)-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine

생성물 1

HCID 99523935-[3-(4-Fluorophenyl)propanoyl]-4-(4-isopropylphenyl)-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine수율 33.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A mixture of histamine dihydrochloride (1.85 g, 10.0 mmol), water (10 mL), potassium hydroxide (1.72 g, 30.0 mmol), ethanol (25 mL) and 4-isopropylbenzaldehyde (1.62 g, 10.91 mmol) was heated to reflux for 1.5 h. Ethanol was evaporated and the residue was diluted with water (40 mL). Extraction (5×25 mL DCM), washing of the combined extracts (2×50 mL brine) and drying (MgSO4) yielded 2.29 g (87%) of crude 4-(4-isopropylphenyl)-4,5,6,7-tetrahydro-imidazo[4,5-c]pyridine, which was used for the next synthetic step without further purification. This amine (0.48 g, 1.99 mmol) was dissolved in DCM (5 mL) and added to a 30 min old mixture of 3-(4-fluorophenyl)propionic acid (0.31 g, 1.84 mmol), HOBt (0.27 g, 1.20 mmol) and EDC (0.42 g, 12.19 mmol) in DCM (10 mL). After 18 h the mixture was washed with water (50 mL), dried (MgSO4) and concentrated. The crude product was purified by column chromatography (silica gel, gradient elution with DCM/methanol). 0.24 g (33%) of the title amide was obtained.

후처리

  1. customwas used for the next synthetic step without further purification
  2. additionadded to a 30 min
  3. washAfter 18 h the mixture was washed with water (50 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography (silica gel, gradient elution with DCM/methanol)

출처 및 근거

ORD 기록
ord-14652588e49a478abc29369bdd106b9f
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06908926B1

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