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

HRID 2108570Notes

Reaction equation

HRID 2108570 reaction equation
[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

Participants

9

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-5e3e14dfbf664f1ebb2b057a179f21cc
Source dataset
uspto-grants-2009_04
Patent number
US07514441B2

Reaction notes

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