Triethylamine → HCID 10832923、化合物

HRID 1698961ノート

反応式

HRID 1698961 の反応式
[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

参加物

6

反応物 3

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

生成物 1

HCID 10832923HCID 10832923、化合物収率 7%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒

反応条件

温度
20 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-4049ee36a9e343f3873f3170fc747b6b
出典データセット
uspto-grants-2002_02
特許番号
US06344459B1

反応ノート

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