Potassium Carbonate → HCID 58180582、化合物

HRID 220358

反応式

HRID 220358 の反応式
[NH2:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:20][CH3:21])[C:9]([C:11]([N:13]([CH:17]3[CH2:19][CH2:18]3)[CH:14]3[CH2:16][CH2:15]3)=[O:12])=[CH:10][C:5]2=[C:4]2[N:22]([CH3:25])[CH:23]=[N:24][C:3]=12.C([N:34]=[C:35]=[S:36])(=O)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].Br.Br[CH2:45][C:46]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][N:49]=1)=O>CC(C)=O>[CH:14]1([N:13]([CH:17]2[CH2:19][CH2:18]2)[C:11]([C:9]2[N:8]([CH2:20][CH3:21])[C:6]3=[N:7][C:2]([NH:1][C:35]4[S:36][CH:45]=[C:46]([C:48]5[CH:53]=[CH:52][CH:51]=[CH:50][N:49]=5)[N:34]=4)=[C:3]4[N:24]=[CH:23][N:22]([CH3:25])[C:4]4=[C:5]3[CH:10]=2)=[O:12])[CH2:16][CH2:15]1

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 68284Benzoyl isothiocyanateHCID 27762312-Bromo-1-(2-pyridinyl)-1-ethanone hydrobromideHCID 581805034-amino-N,N-dicyclopropyl-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide

生成物 1

HCID 58180582HCID 58180582、化合物収率 10%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
60 °C

実験手順

A solution of 4-amino-N,N-dicyclopropyl-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (example 1J, 70 mg, 0.21 mmol) and benzoyl isothiocyanate (36 μl, 0.27 mmol) in acetone (1 ml) was stirred at room temperature for 1.5 h. The solvent was removed in vacuo, the residue was taken up in EtOH (1.5 ml), and K2CO3 (40 mg, 0.290 mmol) was added. The reaction was heated at 60° C. for 3 h. Upon cooling to room temperature, 2-bromo-1-(pyridin-2-yl)ethanone, hydrobromide (139.4 mg, 0.50 mmol) was added and the reaction heated at 80° C. for 24 h. The reaction mixture was cooled to room temperature and concentrated. The residue was purified by silica gel chromatography (0-7% MeOH/dichloromethane). Re-purification by preparative HPLC provided 10.2 mg (10% yield) of N,N-dicyclopropyl-6-ethyl-1-methyl-4-(4-(pyridin-2-yl)thiazol-2-ylamino)-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide as a brown solid.

後処理

  1. customThe solvent was removed in vacuo
  2. temperatureUpon cooling to room temperature
  3. temperaturethe reaction heated at 80° C. for 24 h
  4. temperatureThe reaction mixture was cooled to room temperature
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (0-7% MeOH/dichloromethane)

出典と根拠

ORDレコード
ord-784294f13ca14d49a5ece0fc2b4d2b57
出典データセット
uspto-grants-2012_06
特許番号
US08202881B2

関連ノート

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