Water → ethyl 5-({[4-(cyclopropylmethoxy)phenyl]carbonyl}amino)-1,4-dimethyl-1H-indole-2-carboxylate

HRID 239904ノート

反応式

HRID 239904 の反応式
[CH2:1]([N:3]([CH:7]([CH3:9])[CH3:8])[CH:4]([CH3:6])[CH3:5])C.[CH:10]1([CH2:13][O:14][C:15]2[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=2)[CH2:12][CH2:11]1.[OH2:24].O[N:26]1[C:30]2[CH:31]=CC=[CH:34][C:29]=2N=N1.Cl.C(N=C=NC[CH2:42][CH2:43]N(C)C)C.[OH2:47]>CN(C=O)C.C(OCC)(=O)C.C1COCC1>[CH:10]1([CH2:13][O:14][C:15]2[CH:16]=[CH:17][C:18]([C:19]([NH:26][C:30]3[C:29]([CH3:34])=[C:8]4[C:7](=[CH:9][CH:31]=3)[N:3]([CH3:1])[C:4]([C:6]([O:47][CH2:42][CH3:43])=[O:24])=[CH:5]4)=[O:21])=[CH:22][CH:23]=2)[CH2:11][CH2:12]1

参加物

9

反応物 5

HCID 962WaterHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 226453014-(Cyclopropylmethoxy)benzoic acid

生成物 1

HCID 70968097ethyl 5-({[4-(cyclopropylmethoxy)phenyl]carbonyl}amino)-1,4-dimethyl-1H-indole-2-carboxylate収率 90%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Ethyl 5-amino-1,4-dimethyl-1H-indole-2-carboxylate hydrochloride (400 mg) obtained in Reference Example 45 was suspended in DMF (4.0 mL), ethyldiisopropylamine (0.25 mL), 4-(cyclopropylmethoxy)benzoic acid (300 mg), 1-hydroxybenzotriazole monohydrate (456 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (568 mg) and N,N-dimethylaminopyridine (200 mg) were successively added, and the mixture was stirred at room temperature for 22 hr. After dilution with THF and ethyl acetate, water was added. The organic layer was washed twice with water, and concentrated under reduced pressure. The residue was suspended in diisopropyl ether, and the precipitate was collected by filtration, washed with diisopropyl ether, and dried under reduced pressure to give the title compound (547 mg, yield 90%) as a white solid.

後処理

  1. washThe organic layer was washed twice with water
  2. concentrationconcentrated under reduced pressure
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with diisopropyl ether
  5. customdried under reduced pressure

出典と根拠

ORDレコード
ord-80be2a56bb784e7685f13293bb191226
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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