Sodium Carbonate → [8-(3-Aminomethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyrazin-2-yl]-(3,5-dimethoxy-phenyl)-amine

HRID 570603노트

반응식

HRID 570603 반응식
Cl[C:2]1[C:3]2[N:4]([N:8]=[C:9]([NH:11][C:12]3[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14]([O:20][CH3:21])[CH:13]=3)[N:10]=2)[CH:5]=[CH:6][N:7]=1.[NH2:22][CH2:23][C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:22][CH2:23][C:24]1[CH:29]=[C:28]([C:2]2[C:3]3[N:4]([N:8]=[C:9]([NH:11][C:12]4[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14]([O:20][CH3:21])[CH:13]=4)[N:10]=3)[CH:5]=[CH:6][N:7]=2)[CH:27]=[CH:26][CH:25]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 2773203(3-(Aminomethyl)phenyl)boronic acidHCID 86694342(8-Chloro-[1,2,4]triazolo[1,5-a]pyrazine-2-yl]-(3,5-dimethoxy-phenyl)-amine

생성물 1

HCID 66583836[8-(3-Aminomethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyrazin-2-yl]-(3,5-dimethoxy-phenyl)-amine

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

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온도
120 °C

실험 절차

To a solution of (8-chloro-[1,2,4]triazolo[1,5-a]pyrazine-2-yl]-(3,5-dimethoxy-phenyl)-amine (0.2 g, 0.65 mmol, 1 eq) in a mixture of dimethoxy ethane (3 ml) and water (1 ml), 3-aminomethylphenyl boronic acid (0.28 g, 1.31 mmol, 2 eq), sodium carbonate (0.14 g, 1.31 mmol, 2 eq)) and dichlorobis(triphenyl-phospine)palladium (II) (0.023 g, 0.03 mmol, 5%) are taken in a microwave vial and heated at 120° C. for 2 hours. The reaction mixture is concentrated and the residue is taken in dichloromethane (10 ml×1), washed with brine solution (10 ml×1), the organic layer is dried over anhydrous MgSO4 and concentrated. The crude product obtained is purified by silica gel column using (230-400) mesh to get the titled product as yellow solid.

후처리

  1. concentrationThe reaction mixture is concentrated
  2. washwashed with brine solution (10 ml×1)
  3. dry with materialthe organic layer is dried over anhydrous MgSO4
  4. concentrationconcentrated
  5. customThe crude product obtained
  6. customis purified by silica gel column

출처 및 근거

ORD 기록
ord-b6dec6b7854a4deab300a40132862a9f
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09023851B2

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