Potassium Carbonate → HCID 70675711, 화합물

HRID 628956

반응식

HRID 628956 반응식
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10](Br)=[CH:11][CH:12]=2)[C@H:7]([NH:15][C:16]2[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][N:17]=2)[CH2:6][C@@H:5]1[CH3:24])(=[O:3])[CH3:2].[CH3:25][O:26][CH2:27][CH2:28][N:29]1[CH:33]=[C:32](B2OC(C)(C)C(C)(C)O2)[CH:31]=[N:30]1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:32]3[CH:31]=[N:30][N:29]([CH2:28][CH2:27][O:26][CH3:25])[CH:33]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:15][C:16]2[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][N:17]=2)[CH2:6][C@@H:5]1[CH3:24])(=[O:3])[CH3:2]

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 112304911-(2-Methoxyethyl)-1H-pyrazole-4-boronic acid, pinacol esterHCID 70977959HCID 70977959, 화합물

생성물 1

HCID 70675711HCID 70675711, 화합물

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매2회

반응 조건

온도
120 °C

실험 절차

A microwaveable vial was charged with 6-(((2S,4R)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)amino)nicotinonitrile (for a preparation see Intermediate 6) (74 mg, 0.192 mmol), 1-(2-methoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (CAS No. 847818-71-7 available from Milestone PharmTech USA Inc.) (63 mg, 0.250 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (21 mg, 0.029 mmol), potassium carbonate (56 mg, 0.405 mmol), water (0.5 ml), and 1,4-dioxane (1.5 ml). The vial was sealed and heated at 120° C. for 30 min (microwave). The reaction solution was diluted with water (10 ml), extracted with ethyl acetate (3×15 ml). The organics were combined, dried (hydrophobic frit). The solvent was evaporated in vacuo. The residue was dissolved in methanol/DMSO (1:1, 1 ml) and purified by MDAP (TFA). The solvent was evaporated under a stream of nitrogen, the residue was redissolved in methanol and filtered through an aminopropyl SPE (2 g). The solvent was evaporated in vacuo, to give 6-(((2S,4R)-1-acetyl-6-(1-(2-methoxyethyl)-1H-pyrazol-4-yl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)amino)nicotinonitrile (40 mg) as a white solid.

후처리

  1. customThe vial was sealed
  2. extractionextracted with ethyl acetate (3×15 ml)
  3. customdried (hydrophobic frit)
  4. customThe solvent was evaporated in vacuo
  5. dissolutionThe residue was dissolved in methanol/DMSO (1:1, 1 ml)
  6. custompurified by MDAP (TFA)
  7. customThe solvent was evaporated under a stream of nitrogen
  8. dissolutionthe residue was redissolved in methanol
  9. filtrationfiltered through an aminopropyl SPE (2 g)
  10. customThe solvent was evaporated in vacuo

출처 및 근거

ORD 기록
ord-30abe7b148184ffdab21b503818bf620
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315487B2

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