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Dicyclohexylcarbodiimide → 3-[4-[2-(1-Pyrrolidinyl)ethoxy]benzyl]-2-[4-[1-oxo-2-(1,1-dioxothiomorpholin-4-yl)ethylamino]phenyl]benzo[b]thiophene

HRID 1070349
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HRID 1070349 반응식
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:31]=[CH:30][C:12]([CH2:13][C:14]3[C:15]4[CH:29]=[CH:28][CH:27]=[CH:26][C:16]=4[S:17][C:18]=3[C:19]3[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=3)=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[O:32]=[S:33]1(=[O:43])[CH2:38][CH2:37][N:36]([CH2:39][C:40](O)=[O:41])[CH2:35][CH2:34]1.C1CCC(N=C=NC2CCCCC2)CC1.C1C=NC2N(O)N=NC=2C=1>CN(C=O)C.[Cl-].[Na+].O>[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:31]=[CH:30][C:12]([CH2:13][C:14]3[C:15]4[CH:29]=[CH:28][CH:27]=[CH:26][C:16]=4[S:17][C:18]=3[C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:40](=[O:41])[CH2:39][N:36]4[CH2:37][CH2:38][S:33](=[O:43])(=[O:32])[CH2:34][CH2:35]4)=[CH:21][CH:20]=3)=[CH:11][CH:10]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 181649HOAtHCID 28062362-(1,1-Dioxo-1lambda6-thiomorpholin-4-yl)acetic acidHCID 224627922-(4-Aminophenyl)-3-[4-(2-(1-pyrrolidinyl)ethoxy]benzyl]benzo[b]thiophene

생성물 1

HCID 211830213-[4-[2-(1-Pyrrolidinyl)ethoxy]benzyl]-2-[4-[1-oxo-2-(1,1-dioxothiomorpholin-4-yl)ethylamino]phenyl]benzo[b]thiophene수율 92.3%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

실험 절차

3-[4-[2-(1-Pyrrolidinyl)ethoxy]benzyl]-2-(4-aminophenyl)benzo[b]thiophene (50 mg) and (1,1-dioxothiomorpholin-4-yl)acetic acid (30 mg) were dissolved in DMF (2.0 mL), treated with DCC (30 mg) and HOAt (28 mg) sequentially, and allowed to stir at ambient temperature under argon for 19 h. The reaction mixture was diluted with brine (30 mL), extracted with ethyl acetate (20 mL×3). The combined organic layers were dried with sodium sulfate and concentrated. Chromatography with Et3N:MeOH:EtOAc (5:5:90) afforded the title compound (65 mg).

후처리

  1. extractionextracted with ethyl acetate (20 mL×3)
  2. dry with materialThe combined organic layers were dried with sodium sulfate
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e9fea735215647588b021fab1153128c
출처 데이터셋
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06251921B1

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