Dichloromethane → Benzyl 4-(4-chloro-5-trifluoromethylpyrimidin-2-ylamino)-benzoate

HRID 467802

반응식

HRID 467802 반응식
[NH2:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.Cl[C:28]1[N:33]=[C:32]([Cl:34])[C:31]([C:35]([F:38])([F:37])[F:36])=[CH:30][N:29]=1.C(Cl)Cl>CC(N(C)C)=O>[Cl:34][C:32]1[C:31]([C:35]([F:37])([F:36])[F:38])=[CH:30][N:29]=[C:28]([NH:1][C:2]2[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:7])=[CH:4][CH:3]=2)[N:33]=1

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 98488Benzyl p-aminobenzoateHCID 27827742,4-Dichloro-5-(trifluoromethyl)pyrimidine

생성물 1

HCID 58809948Benzyl 4-(4-chloro-5-trifluoromethylpyrimidin-2-ylamino)-benzoate

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매2회

반응 조건

온도
60 °C

실험 절차

10 g (44 mmol) benzyl 4-aminobenzoate are dissolved in 200 mL DMA, 8 mL Hünig base (0.97 eq) are added and 10.4 g (48.21 mmol) 2,4-dichloro-5-trifluoromethylpyrimidine, dissolved in 50 mL DMA, are added dropwise at RT to this solution. The reaction mixture is stirred at 60° C. overnight, then combined with 300 mL DCM and extracted with water (3 times 300 mL). The organic phase is dried and the solvent is eliminated in vacuo. The crude product is combined with 100 mL MeOH, digested and left to stand for 2 h. Then it is stirred for 10 min, the precipitate is filtered off and washed with MeOH. Finally the crude product is again suspended in MeOH, filtered off, washed with a little MeOH and dried in the vacuum dryer at 60° C. 8.5 g A-2a are obtained.

후처리

  1. additionare added dropwise at RT to this solution
  2. extractionextracted with water (3 times 300 mL)
  3. customThe organic phase is dried
  4. waitleft
  5. waitto stand for 2 h
  6. stirringThen it is stirred for 10 min
  7. filtrationthe precipitate is filtered off
  8. washwashed with MeOH
  9. filtrationfiltered off
  10. washwashed with a little MeOH
  11. customdried in the vacuum dryer at 60° C
  12. customare obtained

출처 및 근거

ORD 기록
ord-8a32d504900b462eb107f58c27390590
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623887B2

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