Tetrahydrofuran → 3-(1-(4-Prop-2-ynyloxymethyl-benzyl)-1H-pyrazol-4-yl)-pyridin-2-ylamine

HRID 78206노트

반응식

HRID 78206 반응식
[NH:1]1[CH:5]=[C:4]([C:6]2[C:7]([NH2:12])=[N:8][CH:9]=[CH:10][CH:11]=2)[CH:3]=[N:2]1.O1CCCC1.[H-].[Na+].Cl[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][O:29][CH2:30][C:31]#[CH:32])=[CH:24][CH:23]=1>O.CN(C)C=O>[CH2:30]([O:29][CH2:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][N:1]2[CH:5]=[C:4]([C:6]3[C:7]([NH2:12])=[N:8][CH:9]=[CH:10][CH:11]=3)[CH:3]=[N:2]2)=[CH:27][CH:26]=1)[C:31]#[CH:32]

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 592552251-Chloromethyl-4-prop-2-ynyloxymethyl-benzeneHCID 592552903-(1H-pyrazol-4-yl)-pyridin-2-ylamine

생성물 1

HCID 592553613-(1-(4-Prop-2-ynyloxymethyl-benzyl)-1H-pyrazol-4-yl)-pyridin-2-ylamine수율 62%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a mixture of 3-(1H-pyrazol-4-yl)-pyridin-2-ylamine (30 mg, 0.19 mmol) described in Manufacturing Example 32-1-4 and tetrahydrofuran (1 mL) was added sodium hydride (12 mg, 0.24 mmol, 50% in oil) at 0° C., and then N,N-dimethylformamide (1 mL) was added. The reaction mixture was stirred for 10 minutes at room temperature, after which 1-chloromethyl-4-prop-2-ynyloxymethyl-benzene (47 mg, 0.24 mmol) described in Manufacturing Example 194-1-2 was added to this mixture at 0° C., which was stirred for 2 hours at room temperature. Water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and was concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=4:1) to obtain the title compound (37 mg, 62%).

후처리

  1. additionwas added to this mixture at 0° C.
  2. stirringwhich was stirred for 2 hours at room temperature
  3. extractionwas extracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium chloride
  5. concentrationwas concentrated under a reduced pressure
  6. customThe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=4:1)

출처 및 근거

ORD 기록
ord-21c079ac8a17473bad43a83aa92f26c1
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841327B2

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