Triethylamine → 1-(2,4-Dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-amine

HRID 1399121

반응식

HRID 1399121 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:14]2=[N:15][C:16]3[C:17](=[C:18](C(O)=O)[CH:19]=[CH:20][CH:21]=3)[N:13]2[CH2:12][CH2:11][CH2:10]1.C1(P(C2C=CC=CC=2)(=O)O)C=CC=CC=1.C([N:42](CC)CC)C>C(O)(C)(C)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:14]2=[N:15][C:16]3[C:17](=[C:18]([NH2:42])[CH:19]=[CH:20][CH:21]=3)[N:13]2[CH2:12][CH2:11][CH2:10]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 15567Diphenylphosphinic acidHCID 577864031-(2,4-Dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxylic acid

생성물 1

HCID 577861701-(2,4-Dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-amine

시약·촉매·용매 1

HCID 6386tert-Butanol용매

반응 조건

온도
90 °C

실험 절차

A mixture of 1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxylic acid (9.40 g, 25.9 mmol), diphenylphosphinic acid (7.85 g, 28.5 mmol) and triethylamine (4.0 mL) in t-butanol (250 mL) was stirred at 90° C. for 12 hr and concentrated in vacuo. A mixture of the residue and trifluoroacetic acid (100 mL) in dichloromethane (50 mL) was stirred at room temperature for 20 hr and concentrated in vacuo. The residue was diluted with saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 10-60% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the title compound as a yellow amorphous (440 mg, 1.32 mmol, 5%).

후처리

  1. concentrationconcentrated in vacuo
  2. additionA mixture of the residue and trifluoroacetic acid (100 mL) in dichloromethane (50 mL)
  3. stirringwas stirred at room temperature for 20 hr
  4. concentrationconcentrated in vacuo
  5. additionThe residue was diluted with saturated aqueous sodium hydrogen carbonate
  6. extractionextracted with ethyl acetate
  7. washThe combined organic layer was washed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by flash column chromatography on silica gel eluting with a 10-60% ethyl acetate/n-hexane gradient mixture
  12. concentrationThe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-fefa76d2e30245e1bf7f3a4eed5d4b44
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901141B2

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