N-methyl-2-pyrrolidone → 11-[6-(hydroxymethyl)-3-azabicyclo[4.1.0]hept-3-yl]-2,3-dihydro-1H-cyclopenta[4,5]pyrido[1,2-a]benzimidazole-4-carboxamide

HRID 70796노트

반응식

HRID 70796 반응식
Cl[C:2]1[N:10]2[C:6](=[N:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=32)[C:5]([C:15]([NH2:17])=[O:16])=[C:4]2[CH2:18][CH2:19][CH2:20][C:3]=12.CCN(C(C)C)C(C)C.CN1C(=O)CCC1.Cl.[CH:38]12[CH2:44][C:43]1([CH2:45][OH:46])[CH2:42][CH2:41][NH:40][CH2:39]2>O>[OH:46][CH2:45][C:43]12[CH2:44][CH:38]1[CH2:39][N:40]([C:2]1[N:10]3[C:6](=[N:7][C:8]4[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=43)[C:5]([C:15]([NH2:17])=[O:16])=[C:4]3[CH2:18][CH2:19][CH2:20][C:3]=13)[CH2:41][CH2:42]2

참가 물질

6

반응물 4

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 86677058HCID 86677058, 화합물HCID 867626763-Azabicyclo[4.1.0]heptan-6-ylmethanol;hydrochloride

생성물 1

HCID 7126859411-[6-(hydroxymethyl)-3-azabicyclo[4.1.0]hept-3-yl]-2,3-dihydro-1H-cyclopenta[4,5]pyrido[1,2-a]benzimidazole-4-carboxamide수율 74.8%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

11-chloro-2,3-dihydro-1H-cyclopenta[4,5]pyrido[1,2-a]benzimidazole-4-carboxamide (800 mg) and DIPEA (1.95 ml) were added to an NMP suspension of 3-azabicyclo[4.1.0]hept-6-ylmethanol hydrochloride (1.01 g), and stirring was performed at 220° C. for 60 minutes under microwave irradiation. The reaction liquid was added to water and the precipitate was collected by filtration. The resulting solid was purified by silica gel column chromatography (MeOH/chloroform) to obtain 11-[6-(hydroxymethyl)-3-azabicyclo[4.1.0]hept-3-yl]-2,3-dihydro-1H-cyclopenta[4,5]pyrido[1,2-a]benzimidazole-4-carboxamide (788 mg).

후처리

  1. customwas performed at 220° C. for 60 minutes under microwave irradiation
  2. customThe reaction liquid
  3. filtrationthe precipitate was collected by filtration
  4. customThe resulting solid was purified by silica gel column chromatography (MeOH/chloroform)

출처 및 근거

ORD 기록
ord-2d3ceea441bf4ee392c878062fd6aba4
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822688B2

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