Ammonium Chloride → Ethyl 5-(4-(((9H-fluoren-9-yl)methoxy)carbonylamino)phenylthio)-4-aminothiophene-2-carboxylate

HRID 883995노트

반응식

HRID 883995 반응식
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([S:25][C:26]4[S:30][C:29]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:28][C:27]=4[N+:36]([O-])=O)=[CH:21][CH:20]=3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Cl-].[NH4+]>C(O)C.O1CCCC1.O.C(OCC)(=O)C.[Fe]>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([S:25][C:26]4[S:30][C:29]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:28][C:27]=4[NH2:36])=[CH:21][CH:20]=3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

참가 물질

8

반응물 2

HCID 25517Ammonium ChlorideHCID 67040709Ethyl 5-(4-(((9H-fluoren-9-yl)methoxy)carbonylamino)phenylthio)-4-nitrothiophene-2-carboxylate

생성물 1

HCID 67040774Ethyl 5-(4-(((9H-fluoren-9-yl)methoxy)carbonylamino)phenylthio)-4-aminothiophene-2-carboxylate수율 80.5%

시약·촉매·용매 5

HCID 23925Iron촉매HCID 702Ethanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of the product of Example 90C (0.918 g, 1.679 mmol) in ethanol (14 mL) and tetrahydrofuran (14 mL) was treated with iron powder (0.577 g, 10.33 mmol) and a solution of ammonium chloride (0.588 g, 10.99 mmol) in water (7 mL), then refluxed for one hour. The reaction was cooled, diluted with ethyl acetate (100 mL), and washed with water (3×25 mL) and brine (25 mL). The organic extract was dried over sodium sulfate, filtered, and concentrated by rotary evaporation to afford the title compound as a yellow solid (0.698 g, 1.351 mmol, 80%). 1H NMR (300 MHz, DMSO-D6) δ ppm 1.27 (t, J=6.99 Hz, 3 H) 4.19-4.36 (m, 3 H) 4.48 (d, J=6.62 Hz, 2 H) 5.56 (s, 2 H) 7.10 (d, J=8.09 Hz, 2 H) 7.28-7.55 (m, 7 H) 7.74 (d, J=7.35 Hz, 2 H) 7.90 (d, J=7.35 Hz, 2 H) 9.73 (s, 1 H); MS (ESI+) m/z 517 (M+H)+, 539 (M+Na)+.

후처리

  1. temperatureThe reaction was cooled
  2. washwashed with water (3×25 mL) and brine (25 mL)
  3. extractionThe organic extract
  4. dry with materialwas dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation

출처 및 근거

ORD 기록
ord-5c64e275ade4468e8bab07426fbb4745
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08236950B2

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