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Ethyl formimidate hydrochloride → N-[4-(2-{4-[(iminomethyl)amino]phenyl)ethyl)-1,3-thiazol-2-yl]acetamide

HRID 1246512
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HRID 1246512 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[N:11]=[C:12]([NH:15][C:16](=[O:18])[CH3:17])[S:13][CH:14]=2)=[CH:4][CH:3]=1.Cl.[CH:20](=[NH:24])OCC>C1COCC1>[NH:24]=[CH:20][NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[N:11]=[C:12]([NH:15][C:16](=[O:18])[CH3:17])[S:13][CH:14]=2)=[CH:4][CH:3]=1
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참가 물질

4

반응물 2

HCID 12578842Ethyl formimidate hydrochlorideHCID 21914814N-{4-[2-(4-aminophenyl)ethyl]thiazol-2-yl}acetamide

생성물 1

HCID 178474436N-[4-(2-{4-[(iminomethyl)amino]phenyl)ethyl)-1,3-thiazol-2-yl]acetamide수율 66.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

N-(4-[2-(4-Aminophenyl)ethyl]-1,3-thiazol-2-yl)acetamide (150 mg) was dissolved in THF (2 ml) and pH=7 buffer (2 ml). Then, ethyl imidoformate hydrochloride (1.26 g) was added to the solution at 0° C. The reaction mixture was stirred at 0° C. for 2 hours, and concentrated in vacuo. The residue was purified by flash column chromatography over silica gel with CH3CN/water (7:3) as an eluent. The oil was purified again by preparative silica gel chromatography with CHCl3/MeOH (5:1) as an eluent to give N-[4-(2-{4-[(iminomethyl)amino]phenyl}ethyl)-1,3-thiazol-2-yl]acetamide (110 mg) as pale brown oil.

후처리

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by flash column chromatography over silica gel with CH3CN/water (7:3) as an eluent
  3. customThe oil was purified again by preparative silica gel chromatography with CHCl3/MeOH (5:1) as an eluent

출처 및 근거

ORD 기록
ord-45cce51a0d6d4d5088b77785cb9866ec
출처 데이터셋
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07125901B2

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