Hydrochloric Acid → 2-(1-{4-[3-(1-methyl-1H-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}-3-oxocyclobutyl)-1H-isoindole-1,3(2H)-dione

HRID 221980노트

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HRID 221980 반응식
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:19]3[C:10]([C:11]4[CH:12]=[C:13]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)[C:14]([C:20]5[CH:25]=[CH:24][C:23]([C:26]6([NH2:34])[CH2:29][C:28]7(OCC[O:30]7)[CH2:27]6)=[CH:22][CH:21]=5)=[N:15][C:16]=4[CH:17]=[CH:18]3)=[N:9][N:8]=2)[N:4]=[CH:3]1.[O:41]=[C:42]1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[C:44](=[O:51])N1C(OCC)=O.CCN(C(C)C)C(C)C.Cl>C(Cl)(Cl)Cl.CO.CN(C=O)C>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:19]3[C:10]([C:11]4[CH:12]=[C:13]([C:35]5[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=5)[C:14]([C:20]5[CH:21]=[CH:22][C:23]([C:26]6([N:34]7[C:42](=[O:41])[C:50]8[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=8)[C:44]7=[O:51])[CH2:29][C:28](=[O:30])[CH2:27]6)=[CH:24][CH:25]=5)=[N:15][C:16]=4[CH:17]=[CH:18]3)=[N:9][N:8]=2)[N:4]=[CH:3]1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 31187N-CarbethoxyphthalimideHCID 81531DiisopropylethylamineHCID 248095872-{4-[3-(1-methyl-1H-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}-5,8-dioxaspiro[3.4]octan-2-amine

생성물 1

HCID 582298522-(1-{4-[3-(1-methyl-1H-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}-3-oxocyclobutyl)-1H-isoindole-1,3(2H)-dione

시약·촉매·용매 3

HCID 887Methanol용매HCID 6212Chloroform용매HCID 6228Dimethylformamide용매

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온도
70 °C

실험 절차

A mixture of 2-{4-[3-(1-methyl-1H-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}-5,8-dioxaspiro[3.4]octan-2-amine (142) (1.3 g, 2.49 mmol) and ethyl 1,3-dioxo-1,3-dihydro-2H-isoindole-2-carboxylate (0.37 g, 2.49 mmol) in CHCl3 (5 mL) was stirred at 70° C. for overnight. The mixture and DMF (5 mL) and DIPEA (0.44 mL, 2.49 mmol) were heated under microwave irradiation at 150° C. for 1 hour. The solvent was removed under reduced pressure, and to the residue was added MeOH. The resulting solid was collected by filtration. The solid (100 mg, 0.152 mmol) and 6N HCl in MeOH (1 mL) was stirred at room temperature for 1 hour. The mixture was quenched by aq. NaHCO3, extracted with CHCl3, dried (MgSO4), filtered, and concentrated under reduced pressure to yield (2-(1-{4-[3-(1-methyl-1H-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}-3-oxocyclobutyl)-1H-isoindole-1,3(2H)-dione (1-13). MS (M+H)+: observed 616, calculated=616.

후처리

  1. customThe solvent was removed under reduced pressure
  2. additionto the residue was added MeOH
  3. filtrationThe resulting solid was collected by filtration
  4. customThe mixture was quenched by aq. NaHCO3
  5. extractionextracted with CHCl3
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-e845706c4d27457e82230666d54f3e11
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207169B2

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