Hydrochloric Acid → 5-(4-Cyclopropyl-2-fluoro-phenylamino)-imidazo[1,5-a]pyridine-6-carboxylic acid (2-hydroxy-ethoxy)-amide

HRID 1500731Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1500731
C([O:3][CH2:4][CH2:5][O:6][NH:7][C:8]([C:10]1[CH:11]=[CH:12][C:13]2[N:14]([CH:27]=[N:28][CH:29]=2)[C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]2[CH2:25][CH2:24]2)=[CH:19][C:18]=1[F:26])=[O:9])=C.Cl>CO>[OH:3][CH2:4][CH2:5][O:6][NH:7][C:8]([C:10]1[CH:11]=[CH:12][C:13]2[N:14]([CH:27]=[N:28][CH:29]=2)[C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]2[CH2:24][CH2:25]2)=[CH:19][C:18]=1[F:26])=[O:9]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 591401465-(4-Cyclopropyl-2-fluoro-phenylamino)-imidazo[1,5-a]pyridine-6-carboxylic acid (2-vinyloxy-ethoxy)-amide

Produkt 1

HCID 441359805-(4-Cyclopropyl-2-fluoro-phenylamino)-imidazo[1,5-a]pyridine-6-carboxylic acid (2-hydroxy-ethoxy)-amideAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 5-(4-cyclopropyl-2-fluoro-phenylamino)-imidazo[1,5-a]pyridine-6-carboxylic acid (2-vinyloxy-ethoxy)-amide (270 mg, 0.681 mmol) in methanol (10 mL) was added 1M hydrochloric acid (2 mL, 2 mmol.) and the mixture stirred at room temperature for 2 hours. Solvent was removed in vacuo, and then saturated aqueous NaHCO3 added and the mixture extracted with ethyl acetate. The organic layer was separated, dried (Na2SO4), filtered and concentrated in vacuo. The resultant residue was triturated with TBME and the solid collected by filtration to give the title compound as an off-white solid (103 mg, 41%). LCMS (Method A): RT 5.68 [M+H]+371. 1H NMR (DMSO-d6, 400 MHz) 7.81 (1 H, s), 7.37-7.34 (1 H, m), 7.27 (1 H, d, J=9.37 Hz), 6.95 (1 H, d, J=9.34 Hz), 6.91 (1 H, dd, J=12.49, 1.92 Hz), 6.75 (1 H, dd, J=8.27, 1.96 Hz), 6.56-6.46 (1 H, m), 3.71-3.65 (2 H, m), 3.48-3.43 (2 H, m), 1.89-1.80 (1 H, m), 0.91-0.85 (2 H, m), 0.65-0.57 (2 H, m).

Aufarbeitung

  1. customSolvent was removed in vacuo
  2. additionsaturated aqueous NaHCO3 added
  3. extractionthe mixture extracted with ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resultant residue was triturated with TBME
  9. filtrationthe solid collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-851c7e7c4e08459496dca64f449bc0d4
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206174B2

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