Triethylamine → N-({4-bromo-6-[(methylcarbamoyl)amino]pyridin-2-yl}carbamoyl)-5-methylthiophene-3-sulfonamide

HRID 1696729ノート

反応式

HRID 1696729 の反応式
[CH3:1][C:2]1[S:6][CH:5]=[C:4]([S:7]([NH2:10])(=[O:9])=[O:8])[CH:3]=1.[C:11]1([O:17]C(Cl)=O)C=CC=CC=1.C(N(CC)CC)C.[NH2:28][C:29]1[N:34]=[C:33]([NH:35][C:36]([NH:38][CH3:39])=[O:37])[CH:32]=[C:31]([Br:40])[CH:30]=1>C(#N)C>[Br:40][C:31]1[CH:32]=[C:33]([NH:35][C:36](=[O:37])[NH:38][CH3:39])[N:34]=[C:29]([NH:28][C:11]([NH:10][S:7]([C:4]2[CH:3]=[C:2]([CH3:1])[S:6][CH:5]=2)(=[O:9])=[O:8])=[O:17])[CH:30]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 572350435-Methylthiophene-3-sulfonamideHCID 672739201-(6-Amino-4-bromo-pyridin-2-yl)-3-methyl-urea

生成物 1

HCID 42629272N-({4-bromo-6-[(methylcarbamoyl)amino]pyridin-2-yl}carbamoyl)-5-methylthiophene-3-sulfonamide収率 35.5%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
0 °C

実験手順

To a solution of 0.089 g 5-methyl-thiophene-3-sulfonic acid amide (example 2a) in 4 ml acetonitrile was added at 0° C. 0.094 g phenylchloroformate and 0.127 g triethylamine. The mixture was stirred at 0° C. for 1 h. To the resulting suspension was added 0.127 g 1-(6-amino-4-bromo-pyridin-2-yl)-3-methyl-urea and the mixture was heated to 60° C. for 18 h. The reaction mixture was partitioned between water and ethyl acetate. The phases were separated and the pH of the aqueous phase was adjusted to 2 by addition of 1N hydrochloric acid. The product was extracted with ethyl acetate. The organic phase was washed with water and brine, dried over sodium sulfate and evaporated to yield 0.080 g of the title compound as an orange yellow powder. MS (ISN) M−H+=445.8 and 447.7

後処理

  1. temperaturethe mixture was heated to 60° C. for 18 h
  2. customThe reaction mixture was partitioned between water and ethyl acetate
  3. customThe phases were separated
  4. additionthe pH of the aqueous phase was adjusted to 2 by addition of 1N hydrochloric acid
  5. extractionThe product was extracted with ethyl acetate
  6. washThe organic phase was washed with water and brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated

出典と根拠

ORDレコード
ord-98a83099f6de41859c9b67a827dc0ce4
出典データセット
uspto-grants-2012_04
特許番号
US08163778B2

反応ノート

読み込み中…