Water → N4-(1H-indazol-6-yl)-N2-(4-(methylthio)phenyl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine

HRID 645686

반응식

HRID 645686 반응식
Cl[C:2]1[N:3]=[C:4]([NH:21][C:22]2[CH:30]=[C:29]3[C:25]([CH:26]=[N:27][NH:28]3)=[CH:24][CH:23]=2)[C:5]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:6]=2[N:7]=1.[CH3:31][S:32][C:33]1[CH:39]=[CH:38][C:36]([NH2:37])=[CH:35][CH:34]=1.C[Si](Cl)(C)C.O>C(O)CCC.C(OCC)(=O)C>[NH:28]1[C:29]2[C:25](=[CH:24][CH:23]=[C:22]([NH:21][C:4]3[C:5]4[CH:10]=[CH:9][N:8]([S:11]([C:14]5[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=5)(=[O:13])=[O:12])[C:6]=4[N:7]=[C:2]([NH:37][C:36]4[CH:38]=[CH:39][C:33]([S:32][CH3:31])=[CH:34][CH:35]=4)[N:3]=3)[CH:30]=2)[CH:26]=[N:27]1

참가 물질

7

반응물 4

HCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 660384-(Methylthio)anilineHCID 866280352-chloro-N-(1H-indazol-6-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

생성물 1

HCID 57585782N4-(1H-indazol-6-yl)-N2-(4-(methylthio)phenyl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine수율 45.5%

시약·촉매·용매 2

HCID 2631-Butanol용매HCID 8857Ethyl Acetate용매

반응 조건

온도
116 °C

실험 절차

A mixture of 2-chloro-N-(1H-indazol-6-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (400 mg, 0.912 mmol), 4-(methylthio)aniline (0.227 mL, 1.83 mmol) and trimethylsilyl chloride (TMSCl) (0.231 mL, 1.83 mmol) in n-butyl alcohol (8 mL) was heated at 116° C. for 72 h. Water and ethyl acetate were then added. The organic phase was separated, washed with 5% NaHCO3, dried over Na2SO4, and concentrated in vacuo. The residue was dissolved in CH3CN (20 mL), and water was added to induced precipitation. The solid was collected by filtration to give N4-(1H-indazol-6-yl)-N2-(4-(methylthio)phenyl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine (225 mg). The filtrate was also purified by HPLC to give another portion of the desired product (127 mg).

후처리

  1. customThe organic phase was separated
  2. washwashed with 5% NaHCO3
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in CH3CN (20 mL)
  6. additionwater was added to induced precipitation
  7. filtrationThe solid was collected by filtration

출처 및 근거

ORD 기록
ord-8a6b4e6e18b543378769ec5d14376460
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07705004B2

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