Methanol → HCID 178493319, 화합물

HRID 387448

반응식

HRID 387448 반응식
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]([NH:9][C:10]2[NH:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=3)=[N:13][N:14]=2)[CH:6]=[CH:7][CH:8]=1.C([O-])([O-])=O.[Cs+].[Cs+].[NH2:30][C:31]1[N:36]=[C:35](Cl)[CH:34]=[C:33]([O:38][CH3:39])[N:32]=1.CO>O1CCOCC1>[CH3:39][O:38][C:33]1[CH:34]=[C:35]([O:21][C:18]2[CH:19]=[CH:20][C:15]([C:12]3[NH:11][C:10]([NH:9][C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:22])([F:1])[F:23])[CH:4]=4)=[N:14][N:13]=3)=[CH:16][CH:17]=2)[N:36]=[C:31]([NH2:30])[N:32]=1

참가 물질

6

반응물 4

HCID 887MethanolHCID 10796Cesium carbonateHCID 798112-Pyrimidinamine, 4-chloro-6-methoxy-HCID 178515914HCID 178515914, 화합물

생성물 1

HCID 178493319HCID 178493319, 화합물수율 40.5%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

4-(5-{[3-(trifluoromethyl)phenyl]amino}-4H-1,2,4-triazol-3-yl)phenol (100 mg, 0.31 mmol) was dissolved in 3 mL of anhydrous dioxane in 2-5 mL microwave vial (Personal Chemistry). Solid Cs2CO3 (101.7 mg, 0.31 mmol) was added, followed by 2-amino-4-chloro-6-methoxypyrimidine (55.0 mg, 0.34 mmol). The vial was capped and microwaved at 200° C. for 15 min. Then ca. 3 mL of MeOH was added to dissolve the formed suspension. The resulting reddish-brown solution was transferred into a round-bottom flask and solvent was removed in vacuo. The residue was re-dissolved in 3 mL of DMF, filtered through 0.22 u syringe filter and purified by reverse phase preparative HPLC using acetonitrile/water system with 0.01% of TEA. The fractions, containing the product, were collected and partitioned between EtOAc and saturated aqueous NaHCO3. Ethyl acetate layer was washed with brine, dried over anhydrous sodium sulfate and filtered. Solvent was removed in vacuo to give the title compound as an off-white solid (55.6 mg).

후처리

  1. customThe vial was capped
  2. custommicrowaved at 200° C. for 15 min
  3. dissolutionto dissolve the formed suspension
  4. customThe resulting reddish-brown solution was transferred into a round-bottom flask
  5. customsolvent was removed in vacuo
  6. dissolutionThe residue was re-dissolved in 3 mL of DMF
  7. filtrationfiltered through 0.22 u syringe
  8. filtrationfilter
  9. custompurified by reverse phase preparative HPLC
  10. additionThe fractions, containing the product
  11. customwere collected
  12. custompartitioned between EtOAc and saturated aqueous NaHCO3
  13. washEthyl acetate layer was washed with brine
  14. dry with materialdried over anhydrous sodium sulfate
  15. filtrationfiltered
  16. customSolvent was removed in vacuo

출처 및 근거

ORD 기록
ord-276c58e83b464af4a0d4b99842f347c5
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372971B2

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