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

HRID 605937

反応式

HRID 605937 の反応式
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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

反応条件

温度
95 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-6cd305aa6b7140dfb87b95a3e98f61f4
出典データセット
uspto-grants-2011_03
特許番号
US07915256B2

関連ノート

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