Diisopropylethylamine → (5-Bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-[4-(2-morpholin-4-yl-ethoxy)-phenyl]-amine

HRID 605937

반응식

HRID 605937 반응식
CN1CCN(C2C=CC(NC3C4N(N=CN=4)C(C4C=C(C(N)=O)SC=4)=CN=3)=CC=2)CC1.[Br:32][C:33]1[N:38]2[N:39]=[CH:40][N:41]=[C:37]2[C:36](Br)=[N:35][CH:34]=1.[N:43]1([CH2:49][CH2:50][O:51][C:52]2[CH:57]=[CH:56][C:55]([NH2:58])=[CH:54][CH:53]=2)[CH2:48][CH2:47][O:46][CH2:45][CH2:44]1.C(N(CC)C(C)C)(C)C>CC(O)C>[Br:32][C:33]1[N:38]2[N:39]=[CH:40][N:41]=[C:37]2[C:36]([NH:58][C:55]2[CH:56]=[CH:57][C:52]([O:51][CH2:50][CH2:49][N:43]3[CH2:44][CH2:45][O:46][CH2:47][CH2:48]3)=[CH:53][CH:54]=2)=[N:35][CH:34]=1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 64847114-(2-Morpholinoethoxy)anilineHCID 497580225,8-Dibromo-(1,2,4)triazolo(1,5-a)pyrazineHCID 575899284-{8-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl}-thiophene-2-carboxylic acid amide

생성물 1

HCID 57590052(5-Bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-[4-(2-morpholin-4-yl-ethoxy)-phenyl]-amine수율 86.2%

시약·촉매·용매 1

HCID 3776Isopropanol용매

반응 조건

온도
95 °C

실험 절차

According to the procedure described for Compound 6, step 1, 5,8-dibromo-[1,2,4]triazolo[1,5-a]pyrazine (0.5 g, 1.799 mmol), 4-(2-morpholin-4-yl-ethoxy)-phenylamine (0.6 g, 4.5 mmol) and N,N-diisopropylethylamine (0.47 mL, 2.7 mmol) in 2-propanol (6 mL) are stirred at 95° C. overnight. After evaporation of the solvent the residue is dissolved in DCM and washed with water (2×) and brine. The organic layer is dried over MgSO4, filtered and concentrated in vacuo to afford an oil purified by silica gel column chromatography. Elution with a 97:3 mixture DCM:MeOH gives the title compound (650 mg 86%) as a light yellow solid. LCMS: Rt 2.06 nm in (97.7%).

후처리

  1. customAfter evaporation of the solvent the residue
  2. dissolutionis dissolved in DCM
  3. washwashed with water (2×) and brine
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford an oil
  8. custompurified by silica gel column chromatography
  9. washElution with a 97:3 mixture DCM

출처 및 근거

ORD 기록
ord-6cd305aa6b7140dfb87b95a3e98f61f4
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915256B2

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