Dimethylformamide → N-[(2R)-1-Hydroxyhexan-2-yl]-2-methyl-8-(3-methylbutoxy)imidazo[1,2-a]pyridine-3-carboxamide

HRID 1844214Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1844214
[OH:1][C:2]1[C:3]2[N:4]([C:8]([C:12]([NH:14][C@H:15]([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:16][OH:17])=[O:13])=[C:9]([CH3:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:29][CH2:30][CH:31]([CH3:33])[CH3:32].CN(C=O)C>O>[OH:17][CH2:16][C@H:15]([NH:14][C:12]([C:8]1[N:4]2[CH:5]=[CH:6][CH:7]=[C:2]([O:1][CH2:29][CH2:30][CH:31]([CH3:33])[CH3:32])[C:3]2=[N:10][C:9]=1[CH3:11])=[O:13])[CH2:18][CH2:19][CH2:20][CH3:21]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 109241-Iodo-3-methylbutaneHCID 867181768-hydroxy-N-[(2R)-1-hydroxyhexan-2-yl]-2-methylimidazo[1,2-a]pyridine-3-carboxamide

Produkt 1

HCID 86718225N-[(2R)-1-Hydroxyhexan-2-yl]-2-methyl-8-(3-methylbutoxy)imidazo[1,2-a]pyridine-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

100 mg (0.34 mmol) of 8-hydroxy-N-[(2R)-1-hydroxyhexan-2-yl]-2-methylimidazo[1,2-a]-pyridine-3-carboxamide, 246 mg (0.76 mmol) of caesium carbonate and 75 mg (0.38 mmol) of 1-iodo-3-methylbutane were added to 4.9 ml of dry DMF, and the mixture was stirred for 30 min in an oil bath preheated to 60° C. After cooling, about 40 ml of water were added to the reaction mixture and the solution formed was extracted three times with ethyl acetate. The combined organic phases were concentrated and the residue was purified by preparative HPLC (RP18 column, mobile phase: water/methanol gradient with addition of 0.1% TFA). All product-containing fractions were combined and concentrated. Saturated aqueous sodium bicarbonate solution was added to the residue, and the mixture was extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulphate, filtered, concentrated and dried under high vacuum. This gave 82 mg of the target compound (66% of theory, purity 100%).

Aufarbeitung

  1. custompreheated to 60° C
  2. temperatureAfter cooling
  3. customthe solution formed
  4. extractionwas extracted three times with ethyl acetate
  5. concentrationThe combined organic phases were concentrated
  6. customthe residue was purified by preparative HPLC (RP18 column, mobile phase: water/methanol gradient with addition of 0.1% TFA)
  7. concentrationconcentrated
  8. additionSaturated aqueous sodium bicarbonate solution was added to the residue
  9. extractionthe mixture was extracted three times with ethyl acetate
  10. dry with materialThe combined organic phases were dried over sodium sulphate
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-9c8ba9fc6d004ac5b910e504b28d19b3
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946215B2

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