Diisopropylethylamine → N-[4-(5-fluoro-4-indol-1-yl-pyrimidin-2-ylamino)-cyclohexyl]-methanesulfonamide

HRID 1947037Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1947037
Cl[C:2]1[N:7]=[C:6]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)[C:5]([F:17])=[CH:4][N:3]=1.[NH2:18][CH:19]1[CH2:24][CH2:23][CH:22]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[CH2:21][CH2:20]1.CCN(C(C)C)C(C)C>CN1C(=O)CCC1.C(Cl)Cl>[F:17][C:5]1[C:6]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[N:7][C:2]([NH:18][CH:19]2[CH2:24][CH2:23][CH:22]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[CH2:21][CH2:20]2)=[N:3][CH:4]=1

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 18348422N-(4-aminocyclohexyl)methanesulfonamideHCID 866208441-(2-chloro-5-fluoro-pyrimidin-4-yl)-1H-indole

Produkt 1

HCID 59743430N-[4-(5-fluoro-4-indol-1-yl-pyrimidin-2-ylamino)-cyclohexyl]-methanesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

1-(2-Chloro-5-fluoro-pyrimidin-4-yl)-1H-indole (0.095 g, 0.38 mmol), N-(4-amino-cyclohexyl)-methanesulfonamide (0.17 g, 0.76 mmol), and DIEA (0.13 mL, 0.76 mmol) were stirred in NMP (2 mL) at 170° C. for 4.5 hours. The solvent was removed at 100° C. in vacuo to yield an oil which was then dissolved in DCM, washed with cold water and brine, and fried with sodium sulfate. The solvent was removed in vacuo to yield an oil. The product was purified using flash chromatography (SiO2) eluting with 1% MeOH/DCM to obtain N-[4-(5-fluoro-4-indol-1-yl-pyrimidin-2-ylamino)-cyclohexyl]-methanesulfonamide as a white solid (Compound 115, 0.025 g, 16%, mp 270.0-270.5° C.).

Aufarbeitung

  1. customThe solvent was removed at 100° C. in vacuo
  2. customto yield an oil which
  3. washwashed with cold water and brine
  4. customThe solvent was removed in vacuo
  5. customto yield an oil
  6. customThe product was purified
  7. washeluting with 1% MeOH/DCM

Quellen und Nachweise

ORD-Eintrag
ord-b3ed8c13bfda4ed6b6cc371db8ae0e00
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399462B2

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