Hydrochloric Acid → HCID 70073718, 화합물

HRID 54008노트

반응식

HRID 54008 반응식
[ClH:1].Cl.[C:3]([C:6]1[CH:33]=[CH:32][C:9]2[S:10][C:11]([CH2:13][CH:14]([C:20]3[CH:25]=[CH:24][C:23]([O:26][C@H:27]4[CH2:31][CH2:30][NH:29][CH2:28]4)=[CH:22][CH:21]=3)[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:12][C:8]=2[CH:7]=1)(=[NH:5])[NH2:4].Cl.[C:35](=[NH:45])(OCC)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(#N)C1C=CC=CC=1.Cl>C(O)C.C(N(CC)CC)C>[ClH:1].[ClH:1].[C:3]([C:6]1[CH:33]=[CH:32][C:9]2[S:10][C:11]([CH2:13][CH:14]([C:20]3[CH:25]=[CH:24][C:23]([O:26][C@H:27]4[CH2:31][CH2:30][N:29]([C:35](=[NH:45])[C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)[CH2:28]4)=[CH:22][CH:21]=3)[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:12][C:8]=2[CH:7]=1)(=[NH:4])[NH2:5]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 7505BenzonitrileHCID 79249Benzenecarboximidic acid, ethyl ester, hydrochloride (1:1)HCID 70074200HCID 70074200, 화합물

생성물 1

HCID 70073718HCID 70073718, 화합물

시약·촉매·용매 2

HCID 702Ethanol용매2회HCID 8471Triethylamine용매

실험 절차

1.0 g of ethyl 3-(5-amidinobenzo[b]thien-2-yl)-2-[4-[((3S)-3-pyrrolidinyl)oxy]phenyl]propionate dihydrochloride was dissolved in 15 ml of ethanol. To this solution was added 773 mg of ethyl benzimidate hydrochloride which has been prepared by allowing benzonitrile to react with ethanol in the presence of hydrogen chloride. 631 mg of triethylamine was added to the thus prepared solution during stirring under ice cooling, and the mixture was warmed up to room temperature, and stirred for 18 hours. Thereafter, the solvent was distilled off to obtain ethyl 3-(5-amidinobenzo[b]thien-2-yl)-2-[4-[((3S)-1-benzimidoyl-3-pyrrolidinyl)oxy]phenyl]propionate dihydrochloride. The thus obtained ester compound was dissolved in 60 ml of 3N hydrochloric acid and refluxed under heating for 30 minutes. After distilling off the solvent, the resulting residue was subjected to column chromatography using a column packed with a highly porous polymer type synthetic adsorbent (styrene-divinylbenzene polymer: Diaion HP-20) and using a water/acetonitrile mixture as an elution solvent. Fractions of interest were pooled and concentrated, and the resulting residue was subjected to reversed phase high performance liquid chromatography using a column packed with octadecyl-bonded silica gel and using a water/acetonitrile mixture as an elution solvent. Thereafter, the thus eluted fractions of interest were pooled, mixed with dilute hydrochloric acid, and then concentrated to dryness. In this way, 350 mg of the title compound was obtained in the form of a light yellow solid.

후처리

  1. customhas been prepared
  2. stirringstirred for 18 hours
  3. distillationThereafter, the solvent was distilled off

출처 및 근거

ORD 기록
ord-cce14374490b4cbaaaa69cd803bf0c5e
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05620991

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