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Methanesulfonic Acid → 3-Amino-1-(3-(trifluoromethyl)-5,6-dihydro(1,2,4)triazolo(4,3-a)pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butan-1-one

HRID 445954
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 445954
C1COCC1.[BH4-].[Na+].CS(O)(=O)=O.[O:13]=[C:14]([N:28]1[CH2:33][CH2:32][N:31]2[C:34]([C:37]([F:40])([F:39])[F:38])=[N:35][N:36]=[C:30]2[CH2:29]1)[CH:15]=[C:16]([NH2:27])[CH2:17][C:18]1[CH:23]=[C:22]([F:24])[C:21]([F:25])=[CH:20][C:19]=1[F:26]>CC(O)C>[O:13]=[C:14]([N:28]1[CH2:33][CH2:32][N:31]2[C:34]([C:37]([F:40])([F:39])[F:38])=[N:35][N:36]=[C:30]2[CH2:29]1)[CH2:15][CH:16]([NH2:27])[CH2:17][C:18]1[CH:23]=[C:22]([F:24])[C:21]([F:25])=[CH:20][C:19]=1[F:26]
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Komponenten

6

Edukt 4

HCID 6395Methanesulfonic AcidHCID 8028Tetrahydrofuran2×HCID 4311764Sodium borohydrideHCID 534002733-Amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one

Produkt 1

HCID 113066913-Amino-1-(3-(trifluoromethyl)-5,6-dihydro(1,2,4)triazolo(4,3-a)pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

In a 250 mL round bottom flask THF (110 mL) was taken. It was cooled to less than −5° C. and NaBH4 (2.81 g) was added. After that methanesulfonic acid (17.8 g) was added dropwise at less than −5° C. over a period of 1 h. 4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)but-2-en-2-amine (10.0 g) is mixed in a solvent mixture of THF (25 mL) and IPA (11 mL) and added into the reaction mixture, keeping the temperature below 0° C. It was stirred for 4-6 h below 5° C. After usual work-up procedure, product was extracted in a suitable solvent. Extract was washed and dried over anhydrous sodium sulfate. Solvent was evaporated at reduced pressure to obtain the product. (Wt.-9.5 g, % Y-94.5%, % Purity by HPLC-94.6%).

Aufarbeitung

  1. temperatureIt was cooled to less than −5° C.
  2. additionadded into the reaction mixture
  3. customthe temperature below 0° C
  4. extractionAfter usual work-up procedure, product was extracted in a suitable solvent
  5. extractionExtract
  6. washwas washed
  7. dry with materialdried over anhydrous sodium sulfate
  8. customSolvent was evaporated at reduced pressure
  9. customto obtain the product

Quellen und Nachweise

ORD-Eintrag
ord-e53c121a5ef34ef1887be4290aca41fd
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08476437B2

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