Triethylamine → N-[4-[(3-bromophenyl)amino]quinazolin-6-yl]-2-methylacrylamide

HRID 1698955ノート

反応式

HRID 1698955 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2[NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=1.CCN(CC)CC.[C:27](Cl)(=[O:31])[C:28]([CH3:30])=[CH2:29]>C1COCC1.CN(C1C=CN=CC=1)C.C([O-])(O)=O.[Na+]>[Br:19][C:15]1[CH:14]=[C:13]([NH:12][C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([NH:1][C:27](=[O:31])[C:28]([CH3:30])=[CH2:29])[CH:3]=3)[N:8]=[CH:7][N:6]=2)[CH:18]=[CH:17][CH:16]=1

参加物

7

反応物 3

HCID 8471TriethylamineHCID 13528Methacryloyl chloride2 回HCID 5328042N4-(3-Bromophenyl)quinazoline-4,6-diamine

生成物 1

HCID 5328981N-[4-[(3-bromophenyl)amino]quinazolin-6-yl]-2-methylacrylamide収率 32%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 8028Tetrahydrofuran溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a stirred solution of 6-amino-4-[(3-bromophenyl)amino]quinazoline (J Med Chem, 1995;38:3482) (0.50 g, 1.59 mmol) in THF (20 mL) under nitrogen was added Et3N (excess, 1.0 mL), a catalytic amount of DMAP and methacryloyl chloride (1.1 mol eq., 1.75 mmol, 171 μL) dropwise. The reaction was stirred at 25° C. for 1.5 hours over which time two further amounts (50 μL) of methacryloyl chloride were added. The reaction was then diluted with saturated NaHCO3 and extracted with EtOAc. The combined organic extracts were dried over anhydrous Na2SO4, concentrated under reduced pressure and chromatographed on silica gel eluting with CH2Cl2/EtOAc (1:1) to MeOH/CH2Cl2/EtOAc (5:45:50). Recrystallization from EtOAc gave N-[4-[(3-bromophenyl)amino]quinazolin-6-yl]-2-methylacrylamide (195 mg, 32%) as a cream powder, mp 244-245° C.

後処理

  1. additionwere added
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customchromatographed on silica gel eluting with CH2Cl2/EtOAc (1:1) to MeOH/CH2Cl2/EtOAc (5:45:50)
  6. customRecrystallization from EtOAc

出典と根拠

ORDレコード
ord-b59bdf53e9ce42debc347980f65ef264
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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