Dimethylamine → N-{4-[(3-bromophenyl)amino]quinazoline-6-yl}4-(dimethylamino)-2-butenamide

HRID 1069012ノート

反応式

HRID 1069012 の反応式
[CH3:1][NH:2][CH3:3].[Br:4][C:5]1[CH:6]=[C:7]([NH:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([NH:22][C:23](=[O:28])[CH:24]=[CH:25][CH2:26]Br)[CH:20]=3)[N:15]=[CH:14][N:13]=2)[CH:8]=[CH:9][CH:10]=1.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>O1CCCC1.CN(C)C=O>[Br:4][C:5]1[CH:6]=[C:7]([NH:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([NH:22][C:23](=[O:28])[CH:24]=[CH:25][CH2:26][N:2]([CH3:3])[CH3:1])[CH:20]=3)[N:15]=[CH:14][N:13]=2)[CH:8]=[CH:9][CH:10]=1

参加物

7

反応物 4

HCID 674DimethylamineHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 544131234-[(3-Bromophenyl)amino]-6-[(4-bromo-1-oxo-2-buten-1-yl)amino]-quinazoline

生成物 1

HCID 49826478N-{4-[(3-bromophenyl)amino]quinazoline-6-yl}4-(dimethylamino)-2-butenamide収率 44%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Twenty five milliliters of 2N dimethylamine in tetrahydrofuran were stirred and cooled in an ice bath, and a solution of 1.16 g (2.5 mmoles) of 4-Bromo-but-2-enoic acid [4-(3-bromo-phenylamino)-quinazolin-6-yl]-amide in 20 mL of tetrahydrofuran and 10 mL of N,N-dimethylformamide was added dropwise. After stirring for 2 hours, 45 mL of ethyl acetate and 30 mL of saturated aqueous sodium bicarbonate were added, and the layers were separated. The organic layer was extracted with 25 mL of brine, dried over sodium sulfate, and taken to an oil in vacuo. This was chromatographed on silica gel with 1:4 methanol methylene chloride to give 475 mg (44%) of the desired product, which melted at 215-217° C. Mass spectrum (m/e) M+2H 213.4, 214.4. M+H 426.1.

後処理

  1. temperaturecooled in an ice bath
  2. customthe layers were separated
  3. extractionThe organic layer was extracted with 25 mL of brine
  4. dry with materialdried over sodium sulfate
  5. customThis was chromatographed on silica gel with 1:4 methanol methylene chloride

出典と根拠

ORDレコード
ord-a203f332c18c4118913b0ae45579b961
出典データセット
uspto-grants-2001_06
特許番号
US06251912B1

反応ノート

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