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

HRID 63758

반응식

HRID 63758 반응식
[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

참가 물질

9

반응물 5

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

생성물 1

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

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매HCID 516892Sodium Bicarbonate용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-53bd5970fa194c108b523c674152c0cb
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447100B2

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