Potassium Carbonate → HCID 58180582, 화합물

HRID 220358

반응식

HRID 220358 반응식
[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

참가 물질

6

반응물 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

생성물 1

HCID 58180582HCID 58180582, 화합물수율 10%

시약·촉매·용매 1

HCID 180Acetone용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-784294f13ca14d49a5ece0fc2b4d2b57
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202881B2

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