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Hydrochloric Acid → N-Cyclopropyl-3-fluoro-5-[2-(3-hydroxy-2,2-dimethylpropyl)-4-{[(2R)-2-methylpiperazin-1-yl]methyl}-1-oxo-1,2-dihydroisoquinolin-6-yl]-4-methylbenzamide

HRID 906475
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 906475
[CH:1]1([NH:4][C:5]([C:7]2[CH:8]=[C:9]([F:46])[C:10]([CH3:45])=[C:11]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[C:19](=[O:23])[N:18]([CH2:24][C:25]([CH3:29])([CH3:28])[CH2:26][OH:27])[CH:17]=[C:16]4[CH2:30][N:31]3[CH2:36][CH2:35][N:34](C(OC(C)(C)C)=O)[CH2:33][C@H:32]3[CH3:44])[CH:12]=2)=[O:6])[CH2:3][CH2:2]1.Cl>CC(O)C>[CH:1]1([NH:4][C:5](=[O:6])[C:7]2[CH:12]=[C:11]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[C:19](=[O:23])[N:18]([CH2:24][C:25]([CH3:28])([CH3:29])[CH2:26][OH:27])[CH:17]=[C:16]4[CH2:30][N:31]3[CH2:36][CH2:35][NH:34][CH2:33][C@H:32]3[CH3:44])[C:10]([CH3:45])=[C:9]([F:46])[CH:8]=2)[CH2:2][CH2:3]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 67391573(3R)-tert-Butyl 4-((6-(5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl)-2-(3-hydroxy-2,2-dimethylpropyl)-1-oxo-1,2-dihydroisoquinolin-4-yl)methyl)-3-methylpiperazine-1-carboxylate

Produkt 1

HCID 45109830N-Cyclopropyl-3-fluoro-5-[2-(3-hydroxy-2,2-dimethylpropyl)-4-{[(2R)-2-methylpiperazin-1-yl]methyl}-1-oxo-1,2-dihydroisoquinolin-6-yl]-4-methylbenzamideAusbeute 96,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776
Isopropanol
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

(3R)-tert-Butyl 4-((6-(5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl)-2-(3-hydroxy-2,2-dimethylpropyl)-1-oxo-1,2-dihydroisoquinolin-4-yl)methyl)-3-methylpiperazine-1-carboxylate (27 g) was dissolved in 2-propanol (200 mL) and HCl (54.1 mL of a 5-6 N solution in 2-propanol) was added. The reaction was heated at 50° C. for 4 h, cooled to room temperature and stirred overnight. The volatiles were evaporated in vacuo and excess HCl removed by addition of toluene followed by solvent removal in vacuo. Water (300 mL) was added followed by the portionwise addition of sodium bicarbonate (7.15 g) until pH 7. Further sodium bicarbonate (7.15 g) was added portionwise and the mixture extracted with DCM (500 mL+200 mL). The combined organics were washed with brine (250 mL), dried (Na2SO4), filtered and the volatiles evaporated in vacuo to give the title product (22 g).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. customThe volatiles were evaporated in vacuo and excess HCl
  3. customremoved by addition of toluene
  4. customfollowed by solvent removal in vacuo
  5. additionWater (300 mL) was added
  6. additionfollowed by the portionwise addition of sodium bicarbonate (7.15 g) until pH 7
  7. additionFurther sodium bicarbonate (7.15 g) was added portionwise
  8. extractionthe mixture extracted with DCM (500 mL+200 mL)
  9. washThe combined organics were washed with brine (250 mL)
  10. dry with materialdried (Na2SO4)
  11. filtrationfiltered
  12. customthe volatiles evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f2d68b92282b450fb53c5ac36e57cb87
Quelldatensatz
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08012980B2

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