Potassium Carbonate → N-tert-butyl-2-(5-(difluoromethoxy)-1-(4-methyl-4-nitropentyl)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

HRID 246752

反応式

HRID 246752 の反応式
[C:1]([NH:5][C:6]([C:8]1[C:12]2=[N:13][C:14]([C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH:27]([F:29])[F:28])[CH:24]=4)[NH:19][N:18]=3)=[CH:15][N:16]=[C:11]2[N:10]([C:30]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].Cl[CH2:56][CH2:57][CH2:58][C:59]([CH3:64])([N+:61]([O-:63])=[O:62])[CH3:60]>CN(C=O)C>[C:1]([NH:5][C:6]([C:8]1[C:12]2=[N:13][C:14]([C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH:27]([F:29])[F:28])[CH:24]=4)[N:19]([CH2:56][CH2:57][CH2:58][C:59]([CH3:64])([N+:61]([O-:63])=[O:62])[CH3:60])[N:18]=3)=[CH:15][N:16]=[C:11]2[N:10]([C:30]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:9]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 553015211-Chloro-4-methyl-4-nitropentaneHCID 71279313N-tert-butyl-2-(5-(difluoromethoxy)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

生成物 1

HCID 71280547N-tert-butyl-2-(5-(difluoromethoxy)-1-(4-methyl-4-nitropentyl)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide収率 74%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a solution of N-tert-butyl-2-(5-(difluoromethoxy)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (208 mg, 0.35 mmol) in DMF (15 mL) was added K2CO3 (193 mg, 1.4 mmol) and 1-chloro-4-methyl-4-nitropentane (100 mg, 0.59 mmol), after the addition, the reaction mixture was heated to 100° C. with stirring for 4 hours. Then, the mixture was quenched with H2O (25 mL) and product extracted with EtOAc (50 mL). The organic layer was washed with H2O (100 mL), brine (100 mL), dried over Na2SO4 and concentrated under reduced pressure to give N-tert-butyl-2-(5-(difluoromethoxy)-1-(4-methyl-4-nitropentyl)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (200 mg, 69%) as yellow solid, material used in the next step without further purification. LCMS: (M+H)+=772; (M+Na)+=794.0.

後処理

  1. additionafter the addition
  2. customThen, the mixture was quenched with H2O (25 mL) and product
  3. extractionextracted with EtOAc (50 mL)
  4. washThe organic layer was washed with H2O (100 mL), brine (100 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-2e4f3a71d1b14b5fb21d3d4492c64337
出典データセット
uspto-grants-2014_02
特許番号
US08658646B2

関連ノート

読み込み中…