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

HRID 63758

反応式

HRID 63758 の反応式
[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

参加物

9

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-53bd5970fa194c108b523c674152c0cb
出典データセット
uspto-grants-2016_09
特許番号
US09447100B2

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