Triethylamine → HCID 10832923, 화합물

HRID 394748노트

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HRID 394748 반응식
[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[C:8]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=3)=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1.CCN(CC)CC.[C:27](Cl)(=[O:30])[CH:28]=[CH2:29]>CN(C1C=CN=CC=1)C.O>[Br:19][C:15]1[CH:14]=[C:13]([NH:12][C:8]2[C:9]3[CH:10]=[N:11][C:2]([NH:1][C:27](=[O:30])[CH:28]=[CH2:29])=[CH:3][C:4]=3[N:5]=[CH:6][N:7]=2)[CH:18]=[CH:17][CH:16]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 3820597-Amino-4-[(3-bromophenyl)amino]pyrido[4,3-d]pyrimidine

생성물 1

HCID 10832923HCID 10832923, 화합물수율 7%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매

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온도
20 °C

실험 절차

To a stirred solution of 7-amino-4-[(3- bromophenyl)amino]pyrido[4,3-d]pyrimidine (J Med Chem, 1995;38:3780) (140 mg, 0.46 mmol), DMAP (14 mg) and Et3N (excess, 2.0 mL) at 0° C. under N2 was added acryloyl chloride (4.8 mol eq., 182 μL) dropwise over 4 hours. The reaction was then stirred at 20° C. diluted with water and extracted with EtOAc. The combined organic extracts were washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure before being chromatographed on silica gel eluting with MeOH/CH2Cl2/EtOAc (5:45:50), to give N-[4-[(3-bromophenyl)amino]pyrido[4,3-d]pyrimidin-7-yl]-acrylamide (12 mg, 7%) as a cream powder, mp (CH2Cl2/hexane) 215-220° C. (dec).

후처리

  1. extractionextracted with EtOAc
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. custombefore being chromatographed on silica gel eluting with MeOH/CH2Cl2/EtOAc (5:45:50)

출처 및 근거

ORD 기록
ord-539664977271424a9f4c39a705bb7db6
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06602863B1

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