Indole-3-Acetic Acid → 1-methyl-2-(1H-indol-3-yl)methylcarbonylaminomethyl-5-(2'-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepine hydrate

HRID 4179

반응식

HRID 4179 반응식
[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])=[N:5][CH2:4][CH:3]1[CH2:20][NH2:21].[NH:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]([CH2:31][C:32]([OH:34])=[O:33])=[CH:23]1.Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl>[OH2:33].[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])=[N:5][CH2:4][CH:3]1[CH2:20][NH:21][C:32]([CH2:31][C:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[NH:22][CH:23]=1)=[O:34]

참가 물질

5

반응물 3

HCID 802Indole-3-Acetic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 14510005(5-(2-fluorophenyl)-1-methyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-2-yl)methanamine

생성물 1

HCID 201529241-methyl-2-(1H-indol-3-yl)methylcarbonylaminomethyl-5-(2'-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepine hydrate수율 71.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

According to the method of Example 1, 1-methyl-2-aminomethyl-5-(2'-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepine (250 mg, 0.88 mmole) and indole-3-acetic acid (154 mg, 0.88 mmole) were combined with 4 ml of dry methylene chloride, and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (169 mg, 0.88 mmole) was added to this mixture. After pH-adjustment, overnight stirring, dilution and washing, rotoevaporation of the dried extracts of the reaction afforded 290 mg of an oil which was purified by silica gel chromatography (ethyl acetate elution) to give material which was 70% pure by HPLC. Rechromatography (chloroform-ethanol elution, 95:5 v/v) afforded the analytical sample, 93% pure, as a yellow solid.

후처리

  1. additionwas added to this mixture
  2. washdilution and washing

출처 및 근거

ORD 기록
ord-e675a8e1c24342e682f05cf2d84ae06b
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04724237

연결된 노트

불러오는 중…