N-methyl-2-pyrrolidone → AS-1517499

HRID 905682ノート

反応式

HRID 905682 の反応式
CN1C(=O)CCC1.[CH2:8]([NH:15][C:16]1[C:21]([C:22]([NH2:24])=[O:23])=[CH:20][N:19]=[C:18](S(C)(=O)=O)[N:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl.[Cl:30][C:31]1[CH:32]=[C:33]([CH2:38][CH2:39][NH2:40])[CH:34]=[CH:35][C:36]=1[OH:37].C(N(C(C)C)CC)(C)C>O>[CH2:8]([NH:15][C:16]1[C:21]([C:22]([NH2:24])=[O:23])=[CH:20][N:19]=[C:18]([NH:40][CH2:39][CH2:38][C:33]2[CH:34]=[CH:35][C:36]([OH:37])=[C:31]([Cl:30])[CH:32]=2)[N:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

参加物

6

反応物 4

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 230715544-(2-Aminoethyl)-2-chlorophenol hydrochlorideHCID 230715814-(Benzylamino)-2-(methanesulfonyl)pyrimidine-5-carboxamide

生成物 1

HCID 10340781AS-1517499収率 28.7%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
110 °C

実験手順

To 8 ml NMP solution of 750 mg of 4-benzylamino-2-methylsulfonylpyrimidine-5-carboxamide were added 765 mg of 2-(3-chloro-4-hydroxyphenyl)ethylamine hydrochloride and 1.07 ml of diisopropylethylamine, followed by stirring a 110° C. for 1 hour. The reaction mixture was cooled down to room temperature, and then mixed with water and extracted with ethyl acetate. The organic layer was washed with saturated brine, and then the solvent was evaporated. The resulting residue was purified by a silica gel column chromatography (chloroform:methanol:aqueous ammonia) and the resulting crude crystals were recrystallized (methanol-ethyl acetate) to obtain 280 mg of 4-benzylamino-2-{[2-(3-chloro-4-hydroxyphenyl)ethyl]amino}pyrimidine-5-carboxamide as colorless crystals.

後処理

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. customthe solvent was evaporated
  5. customThe resulting residue was purified by a silica gel column chromatography (chloroform:methanol:aqueous ammonia)
  6. customthe resulting crude crystals were recrystallized (methanol-ethyl acetate)

出典と根拠

ORDレコード
ord-979c4cb877124a5ca40ec941e90ff027
出典データセット
uspto-grants-2011_09
特許番号
US08012959B2

反応ノート

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