1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → ethyl 5-({[4-(cyclopropylmethoxy)phenyl]carbonyl}amino)-1-methyl-1H-indole-2-carboxylate

HRID 239896노트

반응식

HRID 239896 반응식
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:5]2.[CH:17]1([CH2:20][O:21][C:22]2[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][CH:23]=2)[CH2:19][CH2:18]1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C.O.C(OCC)(=O)C>[CH:17]1([CH2:20][O:21][C:22]2[CH:23]=[CH:24][C:25]([C:26]([NH:1][C:2]3[CH:3]=[C:4]4[C:8](=[CH:9][CH:10]=3)[N:7]([CH3:11])[C:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:5]4)=[O:27])=[CH:29][CH:30]=2)[CH2:18][CH2:19]1

참가 물질

8

반응물 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 11424506Ethyl 5-amino-1-methyl-1H-indole-2-carboxylateHCID 226453014-(Cyclopropylmethoxy)benzoic acid

생성물 1

HCID 70967959ethyl 5-({[4-(cyclopropylmethoxy)phenyl]carbonyl}amino)-1-methyl-1H-indole-2-carboxylate수율 64%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of ethyl 5-amino-1-methyl-1H-indole-2-carboxylate (2.293 g) and 4-(cyclopropylmethoxy)benzoic acid (1.897 g) in DMF (23 mL) were added 1-hydroxybenzotriazole monohydrate (1.965 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.460 g) and N,N-dimethylaminopyridine (1.326 g), and the mixture was stirred at room temperature for 17 hr. After dilution with ethyl acetate, water was added, and the organic layer was washed successively with 1N hydrochloric acid, 1N aqueous, sodium hydroxide solution and saturated brine, and concentrated under reduced pressure. The residue was suspended in ethyl acetate, and the precipitate was collected by filtration, washed with ethyl acetate, and dried under reduced pressure to give the title compound (2.466 g, yield 64%) as a beige solid.

후처리

  1. washthe organic layer was washed successively with 1N hydrochloric acid, 1N aqueous
  2. concentrationsodium hydroxide solution and saturated brine, and concentrated under reduced pressure
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with ethyl acetate
  5. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-673f5a2c6431435893e80711a3a1d2fa
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642770B2

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