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Acetonitrile → 4-Fluoro-6-methyl-1-[1-(tetrahydro-2H-pyran-4-yl)-4-piperidinyl]-1,3-dihydro-2H-benzimidazol-2-one methanesulfonate

HRID 447787
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 447787
[F:1][C:2]1[C:10]2[NH:9][C:8](=[O:11])[N:7]([CH:12]3[CH2:17][CH2:16][N:15]([CH:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)[CH2:14][CH2:13]3)[C:6]=2[CH:5]=[C:4]([CH3:24])[CH:3]=1.C(#N)C.[CH3:28][S:29]([OH:32])(=[O:31])=[O:30]>C(O)CC>[CH3:28][S:29]([OH:32])(=[O:31])=[O:30].[F:1][C:2]1[C:10]2[NH:9][C:8](=[O:11])[N:7]([CH:12]3[CH2:17][CH2:16][N:15]([CH:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)[CH2:14][CH2:13]3)[C:6]=2[CH:5]=[C:4]([CH3:24])[CH:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6342AcetonitrileHCID 6395Methanesulfonic AcidHCID 16038386Gsk 1034702

Produkt 1

HCID 866189424-Fluoro-6-methyl-1-[1-(tetrahydro-2H-pyran-4-yl)-4-piperidinyl]-1,3-dihydro-2H-benzimidazol-2-one methanesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 10311-PropanolLösungsmittel

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

4-Fluoro-6-methyl-1-[1-(tetrahydro-2H-pyran-4-yl)-4-piperidinyl]-1,3-dihydro-2H-benzimidazol-2-one free base (1.499 mmol, 500 mg, 1 wt) was weighed into a 250 ml round bottomed flask, acetonitrile (95 vol., 47.5 ml) and n-propanol (80 vol., 40 ml) were added, giving a white slurry. Methanesulfonic acid (1 eq, 1.499 mmol, 97 □l) was pipetted into the flask. The contents of the flask were heated using a hot air gun—the slurry dissolved and a white precipitate formed. The precipitate was magnetically stirred at 35° C. for four days under nitrogen. After cooling to ambient temperature, the solid was isolated by vacuum filtration and washed with acetonitrile (10 vol. 5 ml). The white solid was dried under high vacuum at 60° C. for 25 hours. 561 mg, 87%, white solid.

Aufarbeitung

  1. customgiving a white slurry
  2. temperatureThe contents of the flask were heated
  3. dissolutiondissolved
  4. customa white precipitate formed
  5. temperatureAfter cooling to ambient temperature
  6. customthe solid was isolated by vacuum filtration
  7. washwashed with acetonitrile (10 vol. 5 ml)
  8. customThe white solid was dried under high vacuum at 60° C. for 25 hours

Quellen und Nachweise

ORD-Eintrag
ord-5b3ae0325a6a4b5ebf43053483fae67d
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08481566B2

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