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

HRID 899599ノート

反応式

HRID 899599 の反応式
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]

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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 N-(1H-Benzimidazol-2-ylmethyl)-N1-(5,6,7,8-tetrahydro-quinolin-8-yl)-butane-1,4-diamine as a white foam.

後処理

  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)

出典と根拠

ORDレコード
ord-2d66e1dd4f3846c6b4c220faa83bd08a
出典データセット
uspto-grants-2008_04
特許番号
US07354932B2

反応ノート

読み込み中…