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Potassium Carbonate → 3-Bromo-7-{3-[(4-methylpiperazin-1-yl)methyl]phenyl}thieno[3,2-c]pyridin-4-amine

HRID 2390670
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HRID 2390670 반응식
[Br:1][C:2]1[C:6]2[C:7]([NH2:19])=[N:8][CH:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17]Cl)[CH:12]=3)[C:5]=2[S:4][CH:3]=1.[CH3:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C([O-])([O-])=[O:28].[K+].[K+]>COCCOC>[NH4+:8].[OH-:28].[Br:1][C:2]1[C:6]2[C:7]([NH2:19])=[N:8][CH:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][N:24]4[CH2:25][CH2:26][N:21]([CH3:20])[CH2:22][CH2:23]4)[CH:12]=3)[C:5]=2[S:4][CH:3]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 18450777HCID 18450777, 화합물

생성물 2

HCID 14923Ammonium Hydroxide수율 0.1%HCID 184507763-Bromo-7-{3-[(4-methylpiperazin-1-yl)methyl]phenyl}thieno[3,2-c]pyridin-4-amine수율 129.4%

시약·촉매·용매 1

HCID 8071
1,2-Dimethoxyethane
용매

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온도
70 °C

실험 절차

A solution of example 673B (200 mg, 0.5 mmol) in DME (2.5 mL) was treated with N-methylpiperazine (0.3 mL, 2.7 mmol) and K2CO3 (350 mg, 2.5 mmol), heated at 70° C. for 1 hour, allowed to cool to room temperature, and partitioned between water and CH2Cl2. The organic extract was dried (Na2SO4), filtered, and the filtrate was concentrated under reduced pressure. The residue was purified via silica gel chromatography eluting with 10% MeOH in CH2Cl2: 0.1% NH4OH to give 135 mg of the title compound (63% yield). MS (ESI (+)) m/e 416.8, 418.8 (M+H)+.

후처리

  1. temperatureto cool to room temperature
  2. custompartitioned between water and CH2Cl2
  3. extractionThe organic extract
  4. dry with materialwas dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified via silica gel chromatography
  8. washeluting with 10% MeOH in CH2Cl2

출처 및 근거

ORD 기록
ord-935bc85c9cb045cda5f5d8672cd9a2db
출처 데이터셋
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08273736B2

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