Acetone → 1,3-Dimethyl-1H-pyrazole-4-sulfonic acid {2-[3'-(4-methoxymethyl-phenyl)-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-yl]-ethyl}-methyl-amide hydrochloride

HRID 553512ノート

反応式

HRID 553512 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]([CH3:27])[S:17]([C:20]3[C:21]([CH3:26])=[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.[CH3:28][O:29][CH2:30][C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1.C(=O)([O-])[O-].[K+].[K+].CC(C)=O>CC(N(C)C)=O.O.C(OCC)(=O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[ClH:1].[CH3:28][O:29][CH2:30][C:31]1[CH:36]=[CH:35][C:34]([C:2]2[C:3]([N:8]3[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]([CH3:27])[S:17]([C:20]4[C:21]([CH3:26])=[N:22][N:23]([CH3:25])[CH:24]=4)(=[O:19])=[O:18])[CH2:10][CH2:9]3)=[N:4][CH:5]=[CH:6][N:7]=2)=[CH:33][CH:32]=1

参加物

9

反応物 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 37238124-(Methoxymethyl)benzeneboronic acidHCID 866402051,3-Dimethyl-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 673695731,3-Dimethyl-1H-pyrazole-4-sulfonic acid {2-[3'-(4-methoxymethyl-phenyl)-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-yl]-ethyl}-methyl-amide hydrochloride収率 56%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 21534740N,N-Dimethylacetamide--water (1/1)溶媒

反応条件

温度
110 °C

実験手順

Dissolve 1,3-dimethyl-1H-pyrazole-4-sulfonic acid [2-(3′-chloro-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-yl)-ethyl]-methyl-amide (270 mg, 0.652 mmol) in DMA-H2O (10 ml; 3:1 v/v, previously degassed with nitrogen). Add 4-methoxymethylphenyl boronic acid (130 mg, 0.783 mmol), potassium carbonate (216 mg, 1.56 mmol) and tetrakis(triphenylphosphine)palladium (38 mg, 0.0326 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 organic layers with brine and concentrate. Purify by chromatography, eluting with 1:2 hexanes:acetone to afford the free base of the title compound (182 mg, 56% 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 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-ef06884c375a45bd8abce15dfac76025
出典データセット
uspto-grants-2011_11
特許番号
US08048884B2

反応ノート

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