Potassium Carbonate → HCID 11501489, 화합물

HRID 661422노트

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HRID 661422 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[O:13][C:12]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)=[N:11][N:10]=2)=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].Br[C:32]1[CH:33]=[N:34][CH:35]=[N:36][CH:37]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CO>[N:34]1[CH:33]=[C:32]([O:20][C:17]2[CH:18]=[CH:19][C:14]([C:12]3[O:13][C:9]([NH:8][C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)=[N:10][N:11]=3)=[CH:15][CH:16]=2)[CH:37]=[N:36][CH:35]=1

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 783445-BromopyrimidineHCID 3251421Potassium bis(trimethylsilyl)amideHCID 136041855HCID 136041855, 화합물

생성물 1

HCID 11501489HCID 11501489, 화합물수율 33.7%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

4-{5-[(4-chlorophenyl)amino]-1,3,4-oxadiazol-2-yl}phenol (144.0 mg, 0.5 mmol) was dissolved in 3 mL of anhydrous DMF in a 2-5 mL microwave vial (Personal Chemistry). Solid potassium bis(trimethylsilyl)amide (100.0 mg, 0.5 mmol) was added and the reaction mixture was stirred with heating at 80° C. for 10 min, then 5-bromopyrimidine (79.5 mg, 0.5 mmol) was added, followed by anhydrous K2CO3 (34.5 mg, 0.25 mmol). Then the vial was capped and microwaved at 200° C. for 15 min. Then the reaction mixture was diluted with ca. 1 mL of MeOH, filtered through 0.22 um syringe filter and purified by reverse-phase preparative HPLC in acetonitrile/water system with 0.01% TFA. Fractions, containing the product, were partitioned between ca. 40 mL of EtOAc and ca. 40 mL of saturated NaHCO3. EtOAc layer was washed with brine, dried over anhydrous Na2SO4 and filtered. Solvent was removed in vacuo to give the title product as a beige solid (61.6 mg).

후처리

  1. customThen the vial was capped
  2. custommicrowaved at 200° C. for 15 min
  3. filtrationfiltered through 0.22 um syringe
  4. filtrationfilter
  5. custompurified by reverse-phase preparative HPLC in acetonitrile/water system with 0.01% TFA
  6. additionFractions, containing the product
  7. customwere partitioned between ca. 40 mL of EtOAc and ca. 40 mL of saturated NaHCO3
  8. washEtOAc layer was washed with brine
  9. dry with materialdried over anhydrous Na2SO4
  10. filtrationfiltered
  11. customSolvent was removed in vacuo

출처 및 근거

ORD 기록
ord-68c24f6b88ba4c27ba7f850c4a5fd1d0
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084618B2

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