Cyclooctylamine → n-Cyclooctyl-5-phenyl-7-(trifluoromethyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 63758

Reaktionsgleichung

Reaktionsgleichung von HRID 63758
[CH:1]1([NH2:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[F:10][C:11]([F:24])([F:23])[C:12](=O)[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=O.CCN=C=[N:29][CH2:30][CH2:31][CH2:32][N:33](C)C.C1C=CC2N(O)N=[N:42]C=2C=1.CN([CH:49]=[O:50])C>CN(C1C=CN=CC=1)C.C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH:1]1([NH:9][C:49]([C:31]2[CH:30]=[N:29][N:42]3[CH:12]([C:11]([F:24])([F:23])[F:10])[CH2:13][CH:14]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[NH:33][C:32]=23)=[O:50])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

9

Edukt 5

HCID 2903CyclooctylamineHCID 6228DimethylformamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 675894,4,4-Trifluoro-1-phenyl-1,3-butanedioneHCID 757711-Hydroxybenzotriazole

Produkt 1

HCID 136071210n-Cyclooctyl-5-phenyl-7-(trifluoromethyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamideAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

Cyclooctylamine (24 mg, 0.19 mmol) was added to a suspension of compound 1 (0.05 g, 0.16 mmol), WSC (37 mg, 0.19 mmol), HOBt (29 mg, 0.19 mmol) and DMAP (23 mg, 0.19 mmol) in DMF (1.5 mL). The reaction mixture was stirred at room temperature for 14 h, diluted with DCM (0.5 mL) and saturated NaHCO3 solution (0.5 mL), and then separated using PHASE-SEP filtration syringe. The organic layer was concentrated and loaded onto preparative HPLC (Gilson 215 system). The purest fractions were combined to give 64.6 mg (96% yield) of the title compound as a white solid. Reverse Phase LC/MS: CAPCELLPAKCC18UG120, S-3 μm, 2.0×50 mm, UV detection at 220, 8 min. gradient 10-100% Solvent B/A (Solvent A: CH3CN with 0.1% TFA, Solvent B: H2O with 0.1% TFA), 0.5 mL/min. Rt=1.90 min, (96% pure). MS (M+H: 421).

Aufarbeitung

  1. customseparated
  2. concentrationThe organic layer was concentrated and loaded onto preparative HPLC (Gilson 215 system)

Quellen und Nachweise

ORD-Eintrag
ord-53bd5970fa194c108b523c674152c0cb
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447100B2

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