Acetone → N-[4-(4-{2-[Methyl-(1-methyl-1H-pyrazole-4-sulfonyl)-amino]-ethyl}-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-3'-yl)-benzyl]-acetamide hydrochloride

HRID 553513노트

반응식

HRID 553513 반응식
[Cl:1][C:2]1[C:3]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]([CH3:26])[S:17]([C:20]3[CH:21]=[N:22][N:23]([CH3:25])[CH:24]=3)(=[O:19])=[O:18])[CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][N:7]=1.C(N[C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+].CC(C)=O.[CH3:50][C:51]([N:53](C)[CH3:54])=[O:52].O>C(OCC)(=O)C.O>[ClH:1].[CH3:26][N:16]([S:17]([C:20]1[CH:21]=[N:22][N:23]([CH3:25])[CH:24]=1)(=[O:19])=[O:18])[CH2:15][CH2:14][N:11]1[CH2:12][CH2:13][N:8]([C:3]2[C:2]([C:31]3[CH:32]=[CH:33][C:34]([CH2:54][NH:53][C:51](=[O:52])[CH3:50])=[CH:35][CH:36]=3)=[N:7][CH:6]=[CH:5][N:4]=2)[CH2:9][CH2:10]1

참가 물질

8

반응물 5

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 27346574-Acetamidophenylboronic acidHCID 21534740N,N-Dimethylacetamide--water (1/1)HCID 866402031-Methyl-1H-pyrazole-4-sulfonic acid [2-(3'-chloro-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-yl)-ethyl]-methyl-amide

생성물 1

HCID 67366252N-[4-(4-{2-[Methyl-(1-methyl-1H-pyrazole-4-sulfonyl)-amino]-ethyl}-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-3'-yl)-benzyl]-acetamide hydrochloride수율 50%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

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온도
110 °C

실험 절차

Dissolve 1-methyl-1H-pyrazole-4-sulfonic acid [2-(3′-chloro-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-yl)-ethyl]-methyl-amide (200 mg, 0.483 mmol) in DMA-H2O (10 ml; 3:1 v/v, previously degassed with nitrogen). Add 4-acetamidophenyl boronic acid (112 mg, 0.580 mmol), potassium carbonate (160 mg, 1.16 mmol) and tetrakis(triphenyl-phosphine)palladium (28 mg, 0.024 mmol). Heat the reaction mixture at 110° C. for 18 hr. Cool and dilute with ethyl acetate and water. Extract the aqueous layer with ethyl acetate and combine the organic layers. Wash the combined organic layers with brine and concentrate. Purify by chromatography, eluting with 1:2 hexanes:acetone to afford the free base of the title compound (124 mg, 50% yield) as a white foam.

후처리

  1. custom3:1 v/v, previously degassed with nitrogen)
  2. temperatureCool
  3. extractionExtract the aqueous layer with ethyl acetate
  4. washWash the combined organic layers with brine
  5. concentrationconcentrate
  6. customPurify by chromatography
  7. washeluting with 1:2 hexanes

출처 및 근거

ORD 기록
ord-91cc292e872b43b3bb3e68b1a3c106ad
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08048884B2

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