Trifluoroacetic acid → N'-(1H-benzimidazol-2-ylmethyl)-N'-(5,6,7,8-tetrahydroquinolin-8-yl)butane-1,4-diamine

HRID 899744노트

반응식

HRID 899744 반응식
C[Si](C)(C)CCOC[N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[CH2:16][N:17]([CH:23]1[C:32]2[N:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH2:26][CH2:25][CH2:24]1)[CH2:18][CH2:19][CH2:20][CH2:21][NH2:22].FC(F)(F)C(O)=O>C(Cl)Cl>[NH:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[CH2:16][N:17]([CH:23]1[C:32]2[N:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH2:26][CH2:25][CH2:24]1)[CH2:18][CH2:19][CH2:20][CH2:21][NH2:22]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 59694106N1-(1-(2-(trimethylsilyl)ethoxymethyl)-1H-Benzimidazol-2-ylmethyl)-N1-(5,6,7,8-tetrahydro-quinolin-8-yl)-butane-1,4-diamine

생성물 1

HCID 10126019N'-(1H-benzimidazol-2-ylmethyl)-N'-(5,6,7,8-tetrahydroquinolin-8-yl)butane-1,4-diamine수율 66.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of N1-(1-(2-(trimethylsilyl)ethoxymethyl)-1H-Benzimidazol-2-ylmethyl)-N1-(5,6,7,8-tetrahydro-quinolin-8-yl)-butane-1,4-diamine (73 mg, 0.16 mmol) in CH2Cl2 (2 mL) was added trifluoroacetic acid (4 mL) and the resultant solution was stirred at room temperature overnight then concentrated under reduced pressure. The residue was dissolved in CH2Cl2 (10 mL) and water (5 mL) and treated with NaOH (10 M, ˜2 mL) until the aqueous phase was basic (pH 14). The phases were separated and the aqueous phase was extracted with CH2Cl2 (3×10 mL). The combined organic extracts were dried (Na2SO4) and concentrated. Purification of the crude material by radial chromatography on silica gel (1 mm plate, 15:1:1 CH2Cl2—CH3OH—NH4OH) provided 37 mg of N1-(1H-Benzimidazol-2-ylmethyl)-N1-(5,6,7,8-tetrahydro-quinolin-8-yl)-butane-1,4-diamine as a white foam.

후처리

  1. concentrationthen concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in CH2Cl2 (10 mL)
  3. additionwater (5 mL) and treated with NaOH (10 M, ˜2 mL) until the aqueous phase
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with CH2Cl2 (3×10 mL)
  6. dry with materialThe combined organic extracts were dried (Na2SO4)
  7. concentrationconcentrated
  8. customPurification of the crude material by radial chromatography on silica gel (1 mm plate, 15:1:1 CH2Cl2—CH3OH—NH4OH)

출처 및 근거

ORD 기록
ord-bdecd604f5dd411787f661e67b17e953
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07354934B2

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