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Water → 3-Piperidin-1-yl-propane-1-sulfonic acid [4-(8-methyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-amide

HRID 1268695
ノート
印刷プレビュー

反応式

HRID 1268695 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][N:11]3[CH:17]=2)=[CH:4][CH:3]=1.[CH2:18]([N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[CH3:19].ClCC[CH2:28][S:29](Cl)(=[O:31])=[O:30].O.[CH3:34]N(C)C=O>>[CH3:16][C:15]1[C:10]2[N:11]([CH:17]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][S:29]([CH2:28][CH2:19][CH2:18][N:20]4[CH2:23][CH2:24][CH2:34][CH2:22][CH2:21]4)(=[O:31])=[O:30])=[CH:7][CH:6]=3)[N:9]=2)[CH:12]=[CH:13][CH:14]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 5

HCID 962WaterHCID 6228DimethylformamideHCID 8471TriethylamineHCID 154103-Chloropropanesulphonyl chlorideHCID 27710774-{8-Methylimidazo[1,2-a]pyridin-2-yl}aniline

生成物 1

HCID 101364233-Piperidin-1-yl-propane-1-sulfonic acid [4-(8-methyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-amide

反応条件

温度
0 °C

実験手順

To a suspension of the product of Example 27 Step B (195 mg) in N,N-dimethylformamide (2 mL) was added triethylamine (0.12 mL) and the mixture cooled to 0° C. 3-chloropropanesulfonyl chloride (0.11 mL) was added dropwise and the mixture stirred for 1.5 hours before the addition of H2O (2 mL). The reaction mixture was partitioned between H2O (15 mL) and ethyl acetate (15 mL). The aqueous layer was brought to pH=9–10 with saturated sodium bicarbonate solution and extracted with ethyl acetate (2×). The combined organic layers were dried over magnesium sulfate, decanted, and evaporated. The residue was purified via silica gel chromatography (dichloromethane/methanol) to give the title compound (210 mg).

後処理

  1. customThe reaction mixture was partitioned between H2O (15 mL) and ethyl acetate (15 mL)
  2. extractionextracted with ethyl acetate (2×)
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. customdecanted
  5. customevaporated
  6. customThe residue was purified via silica gel chromatography (dichloromethane/methanol)

出典と根拠

ORDレコード
ord-cb3612bb6732452384ded3f2fd50f2a5
出典データセット
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07199117B2

反応ノート

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