2-(1,3-Dioxoisoindolin-2-yl)ethyl trifluoromethanesulfonate → 2-(3-Chloroanilino)-4-[1-(2-phthalimidoethyl)imidazol-5-yl]pyrimidine

HRID 1064307노트

반응식

HRID 1064307 반응식
O([CH2:9][CH2:10][N:11]1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21])S(C(F)(F)F)(=O)=O.[Cl:22][C:23]1[CH:24]=[C:25]([CH:57]=[CH:58][CH:59]=1)[NH:26][C:27]1[N:32]=[C:31]([C:33]2[N:34]=[CH:35][N:36](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:37]=2)[CH:30]=[CH:29][N:28]=1>C(Cl)Cl>[Cl:22][C:23]1[CH:24]=[C:25]([CH:57]=[CH:58][CH:59]=1)[NH:26][C:27]1[N:32]=[C:31]([C:33]2[N:34]([CH2:9][CH2:10][N:11]3[C:15](=[O:16])[C:14]4=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]4[C:12]3=[O:21])[CH:35]=[N:36][CH:37]=2)[CH:30]=[CH:29][N:28]=1

참가 물질

4

반응물 2

HCID 118094652-(1,3-Dioxoisoindolin-2-yl)ethyl trifluoromethanesulfonateHCID 222735042-(3-Chloroanilino)-4-(1-triphenylmethylimidazol-4-yl)pyrimidine

생성물 1

HCID 222735062-(3-Chloroanilino)-4-[1-(2-phthalimidoethyl)imidazol-5-yl]pyrimidine수율 40%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

2-Phthalimidoethyl triflate (660 mg, 2.04 mmol) was added to solution of the 2-(3-chloroanilino)-4-(1-triphenylmethylimidazol-4-yl)pyrimidine Method 2; 1.00 g, 1.95 mmol) in DCM (5 ml) and the reaction mixture stirred for 4 hours. The solvent was removed by evaporation and MeOH (6 ml) and 2M hydrochloric acid (1.5 ml) was added to the residue. The mixture was stirred for 5 minutes, the volatiles were removed by evaporation and the residue partitioned between EtOAc and saturated aqueous sodium hydrogen carbonate solution. The resulting precipitate was collected by filtration, washed with water and EtOAc and dried to give the title compound 350 mg, (40%) as a solid. NMR: 3.81-3.96 (m, 2H), 4.77-4.92 (m, 2H), 6.98 (d, 1H), 7.06 (d, 1H), 7.31 (t, 1H), 7.37 (d, 1H), 7.63-7.80 (m, 6H), 7.92 (s, 1H), 8.27 (d, 1H), 9.50 (s, 1H); m/z: 443.

후처리

  1. customThe solvent was removed by evaporation and MeOH (6 ml) and 2M hydrochloric acid (1.5 ml)
  2. additionwas added to the residue
  3. customthe volatiles were removed by evaporation
  4. customthe residue partitioned between EtOAc and saturated aqueous sodium hydrogen carbonate solution
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed with water and EtOAc
  7. customdried

출처 및 근거

ORD 기록
ord-07c2d75e86964e0281dee757f53057c8
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06969714B2

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