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 221980ノート

反応式

HRID 221980 の反応式
[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

参加物

8

反応物 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

生成物 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

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 6212Chloroform溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e845706c4d27457e82230666d54f3e11
出典データセット
uspto-grants-2012_06
特許番号
US08207169B2

反応ノート

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