Triethylamine → tert-butyl 2-(3-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-ylcarbamoyl)imidazo[1,2-a]pyridine-7-carbonyl)hydrazinecarboxylate

HRID 79325ノート

反応式

HRID 79325 の反応式
[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][C:22]([C:24](O)=[O:25])=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([CH3:34])[N:29]=2)[N:4]=1)[CH3:2].[NH:35]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[NH2:36].Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>CN(C=O)C>[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][C:22]([C:24]([NH:36][NH:35][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[O:25])=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([CH3:34])[N:29]=2)[N:4]=1)[CH3:2]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 70091tert-Butyl carbazateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 672601493-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-ylcarbamoyl)imidazo[1,2-a]pyridine-7-carboxylic acid

生成物 1

HCID 67261092tert-butyl 2-(3-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-ylcarbamoyl)imidazo[1,2-a]pyridine-7-carbonyl)hydrazinecarboxylate収率 60.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To 3-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-ylcarbamoyl)imidazo[1,2-a]pyridine-7-carboxylicacid (250 mg, 0.550 mmol) in DMF (5 mL) was added tert-butyl hydrazinecarboxylate (80.0 mg, 0.605 mmol), N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (116 mg, 0.605 mmol), 1H-benzo[c/][1,2,3]triazol-1-ol hydrate (92.7 mg, 0.605 mmol) and triethylamine (66.8 mg, 0.660 mmol). The reaction mixture was stirred overnight and concentrated under reduced pressure to remove DMF. Silica gel chromatography (DCM/MeOH 10:1) provided tert-butyl 2-(3-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-ylcarbamoyl)imidazo[1,2-a]pyridine-7-carbonyl)hydrazinecarboxylate (188 mg), to which was added TFA/DCM (2 mL/3 mL). The mixture was stirred for 30 minutes and concentrated to give the product as the TFA salt (156 mg).

後処理

  1. concentrationconcentrated under reduced pressure
  2. customto remove DMF

出典と根拠

ORDレコード
ord-f7053042fefc47de97cab82115d7c718
出典データセット
uspto-grants-2014_09
特許番号
US08841455B2

反応ノート

読み込み中…