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 553513ノート

反応式

HRID 553513 の反応式
[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

参加物

8

反応物 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

生成物 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 hydrochloride収率 50%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
110 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-91cc292e872b43b3bb3e68b1a3c106ad
出典データセット
uspto-grants-2011_11
特許番号
US08048884B2

反応ノート

読み込み中…