Acetone → N-{4-[3-(4-{2-[Methyl-(1-methyl-1H-pyrazole-4-sulfonyl)-amino]-ethyl}-piperazin-1-yl)-pyridin-2-yl]-phenyl}-acetamide dihydrochloride

HRID 553518ノート

反応式

HRID 553518 の反応式
[Cl:1][C:2]1[C:7]([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)=[CH:6][CH:5]=[CH:4][N:3]=1.CC1(C)C(C)(C)OB([C:35]2[CH:44]=[CH:43][C:38]([NH:39][C:40](=[O:42])[CH3:41])=[CH:37][CH:36]=2)O1.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].[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:7]2[C:2]([C:35]3[CH:44]=[CH:43][C:38]([NH:39][C:40](=[O:42])[CH3:41])=[CH:37][CH:36]=3)=[N:3][CH:4]=[CH:5][CH:6]=2)[CH2:9][CH2:10]1

参加物

9

反応物 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 27346194'-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)acetanilideHCID 866402101-Methyl-1H-pyrazole-4-sulfonic acid {2-[4-(2-chloro-pyridin-3-yl)-piperazin-1-yl]-ethyl}-methyl-amide

生成物 1

HCID 67366546N-{4-[3-(4-{2-[Methyl-(1-methyl-1H-pyrazole-4-sulfonyl)-amino]-ethyl}-piperazin-1-yl)-pyridin-2-yl]-phenyl}-acetamide dihydrochloride収率 137.8%

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-methyl-1H-pyrazole-4-sulfonic acid {2-[4-(2-chloro-pyridin-3-yl)-piperazin-1-yl]-ethyl}-methyl-amide (230 mg, 0.58 mmol) in DMA-H2O (6 mL; 5:1 v/v, previously degassed with nitrogen). Add 4′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acetanilide (181 mg, 0.69 mmol), potassium carbonate (191 mg, 1.38 mmol) and tetrakis(triphenylphosphine)palladium (33 mg, 0.03 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 (228 mg, 79% yield) as a white solid.

後処理

  1. custom5:1 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-56947c41d9114683a99699ebcb3c7d80
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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