Ammonia → HCID 66726154、化合物

HRID 1042110ノート

反応式

HRID 1042110 の反応式
[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([O:11][C:12]2[CH:13]=[C:14]3[C:18](=[C:19]([O:21][CH:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[CH:20]=2)[NH:17][C:16]([C:28]([OH:30])=O)=[CH:15]3)=[N:9][CH:10]=1)(=[O:4])=[O:3].Cl.C[N:33](C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.N>CN(C)C=O>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([O:11][C:12]2[CH:13]=[C:14]3[C:18](=[C:19]([O:21][CH:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[CH:20]=2)[NH:17][C:16]([C:28]([NH2:33])=[O:30])=[CH:15]3)=[N:9][CH:10]=1)(=[O:3])=[O:4]

参加物

6

反応物 4

HCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 667259135-{[5-(Methylsulfonyl)pyridin-2-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indole-2-carboxylic acid

生成物 1

HCID 66726154HCID 66726154、化合物収率 27.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

A mixture of 5-{[5-(methylsulfonyl)pyridin-2-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indole-2-carboxylic acid (2.5 g), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (2.2 g), 1-hydroxybenzotriazole (1.6 g), and N,N-dimethylformamide (25 mL) was stirred at 50° C. for 30 min. The reaction mixture was cooled to room temperature, 10% aqueous ammonia (4 mL) was added and the mixture was stirred at room temperature for 1.5 hr. The reaction solution was concentrated under reduced pressure, water was added to the residue, and ethyl acetate-tetrahydrofuran was added. The precipitated solid was collected by filtration to give the title compound (0.69 g) as a pale-yellow solid. The filtrate was concentrated under reduced pressure to evaporate the organic solvent. The precipitate was collected by filtration to give the title compound (0.72 g) as a pale-yellow solid (total yield 1.41 g, 64%).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringthe mixture was stirred at room temperature for 1.5 hr
  3. concentrationThe reaction solution was concentrated under reduced pressure, water
  4. additionwas added to the residue, and ethyl acetate-tetrahydrofuran
  5. additionwas added
  6. filtrationThe precipitated solid was collected by filtration

出典と根拠

ORDレコード
ord-072c30ff3904413ca958b8d00876fea0
出典データセット
uspto-grants-2013_10
特許番号
US08557805B2

反応ノート

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