Diisopropylethylamine → (5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-[4-(1-isopropylpiperidin-4-yl)-phenyl]amine

HRID 1366200노트

반응식

HRID 1366200 반응식
C(N(CC)C(C)C)(C)C.[CH:10]([N:13]1[CH2:18][CH2:17][CH:16]([C:19]2[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=2)[CH2:15][CH2:14]1)([CH3:12])[CH3:11].[Br:26][C:27]1[N:32]2[CH:33]=[CH:34][N:35]=[C:31]2[C:30](Br)=[N:29][CH:28]=1>CC(O)C>[Br:26][C:27]1[N:32]2[CH:33]=[CH:34][N:35]=[C:31]2[C:30]([NH:25][C:22]2[CH:21]=[CH:20][C:19]([CH:16]3[CH2:15][CH2:14][N:13]([CH:10]([CH3:12])[CH3:11])[CH2:18][CH2:17]3)=[CH:24][CH:23]=2)=[N:29][CH:28]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 534859495,8-Dibromoimidazo[1,2-a]pyrazineHCID 575900714-(1-Isopropylpiperidin-4-yl)aniline

생성물 1

HCID 59023125(5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-[4-(1-isopropylpiperidin-4-yl)-phenyl]amine

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

N,N-Diisopropylethylamine (360 μL, 2.2 mmol) is added to a mixture of 4-(1-isopropylpiperidin-4-yl)phenylamine (220 mg, 1.0 mmol) and 5,8-dibromoimidazo[1,2-a]pyrazine (280 mg, 1.0 mmol) in iPrOH (5 mL) and heated at reflux for 48 h. The mixture is cooled and the solvent evaporated under reduced pressure to afford an orange-brown solid. This is partitioned between DCM (50 mL) and water (20 mL) and the layers are separated. The organic phase is washed with citric acid (10% aq., 3×25 mL). The combined washings are extracted with DCM (25 mL) and then made basic by addition of NaHCO3 (s). The mixture is extracted with DCM (3×25 mL) and the combined extracts dried over MgSO4 and evaporated. The material is used without further purification.

후처리

  1. temperatureheated
  2. temperatureat reflux for 48 h
  3. temperatureThe mixture is cooled
  4. customthe solvent evaporated under reduced pressure
  5. customto afford an orange-brown solid
  6. customThis is partitioned between DCM (50 mL) and water (20 mL)
  7. customthe layers are separated
  8. washThe organic phase is washed with citric acid (10% aq., 3×25 mL)
  9. extractionThe combined washings are extracted with DCM (25 mL)
  10. additionmade basic by addition of NaHCO3 (s)
  11. extractionThe mixture is extracted with DCM (3×25 mL)
  12. dry with materialthe combined extracts dried over MgSO4
  13. customevaporated
  14. customThe material is used without further purification

출처 및 근거

ORD 기록
ord-6e6bfda52336489ba3c3c91266b46816
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893058B2

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