Acetone → 6-(Aziridin-1-yl)-7-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazole-5,8-dione

HRID 2051034

反応式

HRID 2051034 の反応式
[CH3:1][C:2]1[C:13](=[O:14])[C:6]2[N:7]3[CH2:12][CH2:11][CH2:10][C:8]3=[N:9][C:5]=2[C:4](=[O:15])[CH:3]=1.[CH2:16]1[NH:18][CH2:17]1.CC(C)=O.[K+].[Br-]>CO>[N:18]1([C:3]2[C:4](=[O:15])[C:5]3[N:9]=[C:8]4[CH2:10][CH2:11][CH2:12][N:7]4[C:6]=3[C:13](=[O:14])[C:2]=2[CH3:1])[CH2:16][CH2:17]1

参加物

6

反応物 4

HCID 180AcetoneHCID 9033Aziridine2 回HCID 253877Potassium BromideHCID 102198607-Methyl-2,3-dihydro-1H-pyrrolo[1,2-a] benzimidazole-5,8-dione

生成物 1

HCID 156611736-(Aziridin-1-yl)-7-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazole-5,8-dione

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 35 mg (0.17 mmol) of 26 in 4 mL of dry methanol, chilled at 0° C., was added 0.5 mL of ethyleneimine. The reaction was stirred at 0° for 30 min and then at room temperature for 1 hour. The solvent was removed in vacuo and the red residue flash chromatographed on silica gel using chloroform as the eluant. The purified product was recrystallized from chloroform/hexane: 20.5 mg (48%) yield; mp 192°-194° C. dec.; TLC (acetone), Rf =0.73; IR(KBr pellet) 1674, 1632, 1575, 1518, 1377, 1338, 1315, 1137, 988 cm-1 ; 1H NMR (CDCl3) δ4.17 (2 H, t, J~7 Hz, C(1) methylene), 2.89 (2H, t, J~7 Hz, C(3) methylene), 2.65 (2 H, quintet, J~7 Hz, C(2) methylene): 2.31 (4 H, s, aziridine protons), 2.02 (3 H, s, 7-methyl): mass spectrum (EI mode) m/z 243 (P+), 228 (P+ -methyl). (Anal. Calcd for C13H13N3O2 : C, 64.18; H, 5.34; N, 17.27. Found: C, 64.02; H, 5.21; N, 16.76.

後処理

  1. waitat room temperature for 1 hour
  2. customThe solvent was removed in vacuo
  3. customthe red residue flash chromatographed on silica gel
  4. customThe purified product was recrystallized from chloroform/hexane
  5. custom20.5 mg (48%) yield

出典と根拠

ORDレコード
ord-ebfba3a310b14c0c987f10c23103a77b
出典データセット
uspto-grants-1991_05
特許番号
US05015742

関連ノート

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