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

HRID 467802

反応式

HRID 467802 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒2 回

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8a32d504900b462eb107f58c27390590
出典データセット
uspto-grants-2014_01
特許番号
US08623887B2

関連ノート

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