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

HRID 239896ノート

反応式

HRID 239896 の反応式
[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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-673f5a2c6431435893e80711a3a1d2fa
出典データセット
uspto-grants-2014_02
特許番号
US08642770B2

反応ノート

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