Trifluoroacetic acid → 4-(4-(4-Acetyl-2,6-dimethylphenoxy)-5-benzyl-5H-pyrrolo[3,2-d]pyrimidin-2-ylamino)benzonitrile

HRID 1516857노트

반응식

HRID 1516857 반응식
[CH2:1]([N:8]1[C:16]2[C:15]([O:17][C:18]3[C:23]([CH3:24])=[CH:22][C:21]([C:25](=[O:27])[CH3:26])=[CH:20][C:19]=3[CH3:28])=[N:14][C:13](Cl)=[N:12][C:11]=2[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:30][C:31]1[CH:38]=[CH:37][C:34]([C:35]#[N:36])=[CH:33][CH:32]=1.C(O)(C(F)(F)F)=O>O>[C:25]([C:21]1[CH:22]=[C:23]([CH3:24])[C:18]([O:17][C:15]2[C:16]3[N:8]([CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH:9]=[CH:10][C:11]=3[N:12]=[C:13]([NH:30][C:31]3[CH:38]=[CH:37][C:34]([C:35]#[N:36])=[CH:33][CH:32]=3)[N:14]=2)=[C:19]([CH3:28])[CH:20]=1)(=[O:27])[CH3:26]

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 133964-AminobenzonitrileHCID 576935541-(4-(5-benzyl-2-chloro-5H-pyrrolo[3,2-d]pyrimidin-4-yloxy)-3,5-dimethylphenyl)ethanone

생성물 1

HCID 576936424-(4-(4-Acetyl-2,6-dimethylphenoxy)-5-benzyl-5H-pyrrolo[3,2-d]pyrimidin-2-ylamino)benzonitrile수율 51.7%

시약·촉매·용매 1

HCID 962Water용매

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온도
90 °C

실험 절차

In a sealed tube was added 1-(4-(5-benzyl-2-chloro-5H-pyrrolo[3,2-d]pyrimidin-4-yloxy)-3,5-dimethylphenyl)ethanone (111 mg, 0.27 mmol), 4-aminobenzonitrile (129 mg, 1.1 mmol), TFE (1.7 mL) and TFA (0.2 mL, 2.16 mmol). The reaction mixture was stirred at 90° C. for 16 h. Upon completion of the reaction, the resulting mixture was cooled, diluted with water, and washed with EtOAc. The combined organic layers were washed with NaHCO3 and brine; dried over Na2SO4; filtered; and concentrated in vacuo. The crude product was purified by silica gel column chromatography, eluting with hexanes:ethyl acetate (9:1-100% EtOAc), to give the product as an off-white solid (68 mg, 51%).

후처리

  1. customUpon completion of the reaction
  2. temperaturethe resulting mixture was cooled
  3. washwashed with EtOAc
  4. washThe combined organic layers were washed with NaHCO3 and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationand concentrated in vacuo
  8. customThe crude product was purified by silica gel column chromatography
  9. washeluting with hexanes

출처 및 근거

ORD 기록
ord-04e84c98afee4a6786596d6f72b6a209
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08227601B2

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