Diisopropylethylamine → HCID 67359255, Verbindung

HRID 39437

Reaktionsgleichung

Reaktionsgleichung von HRID 39437
[CH:1]1([C:4]2[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:5]=2[C:6]([OH:8])=O)[CH2:3][CH2:2]1.C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.Cl.Cl.[N:52]1([CH:57]2[CH2:62][CH2:61][O:60][CH2:59][CH:58]2[NH2:63])[CH2:56][CH2:55][CH2:54][CH2:53]1>CN(C)C=O>[CH:1]1([C:4]2[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:5]=2[C:6]([NH:63][CH:58]2[CH:57]([N:52]3[CH2:53][CH2:54][CH2:55][CH2:56]3)[CH2:62][CH2:61][O:60][CH2:59]2)=[O:8])[CH2:2][CH2:3]1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 594384852-Cyclopropyl-4-(trifluoromethyl)benzoic acid2×HCID 673600044-(Pyrrolidin-1-yl)tetrahydro-2H-pyran-3-amine dihydrochloride

Produkt 1

HCID 67359255HCID 67359255, VerbindungAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-Cyclopropyl-4-trifluoromethyl-benzoic acid (intermediate J, 118 mg, 0.513 mmol) was dissolved in 2.5 mL dimethylformamide. N,N-Diisopropyl ethyl amine (338 mg, 2.62 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (195 mg, 0.513 mmol) were added. After 10 minutes of stirring at room temperature trans-(4-pyrrolidin-1-yl-tetrahydro-pyran-3-ylamine dihydrochloride (intermediate 1,187 mg, 0.769 mmol) was added. The reaction mixture was stirred at room temperature overnight. The solvent was evaporated off. The residue was taken up in 2N sodium carbonate solution and ethyl acetate and was extracted three times with ethyl acetate. The combined organic phases were dried on sodium sulfate, filtered and evaporated. Purification of the residue by flash chromatography on silica gel (heptane/ethyl acetate/triethylamine 1:0:0→10:10:1) yielded the title compound as a white solid (121 mg, 62%), MS: m/e=383.3 [(M+H)+].

Aufarbeitung

  1. additionwas added
  2. customThe solvent was evaporated off
  3. extractionethyl acetate and was extracted three times with ethyl acetate
  4. customThe combined organic phases were dried on sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customPurification of the residue by flash chromatography on silica gel (heptane/ethyl acetate/triethylamine 1:0:0→10:10:1)

Quellen und Nachweise

ORD-Eintrag
ord-fac9c8face704ca2b24997f1ae65abf9
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524909B2

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