N-methyl-2-pyrrolidone → AS-1517499

HRID 905682노트

반응식

HRID 905682 반응식
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

참가 물질

6

반응물 4

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

생성물 1

HCID 10340781AS-1517499수율 28.7%

시약·촉매·용매 1

HCID 962Water용매

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온도
110 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-979c4cb877124a5ca40ec941e90ff027
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08012959B2

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