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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
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1268695
[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
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Komponenten

6

Edukt 5

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

Produkt 1

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

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-cb3612bb6732452384ded3f2fd50f2a5
Quelldatensatz
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07199117B2

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