Triethylamine → 2-(7-Chloro-1,8-naphthyridin-2-yl)-3-methoxycarbonylmethylaminocarbonyloxy-isoindolin-1-one

HRID 66341ノート

反応式

HRID 66341 の反応式
[Cl:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([N:12]3[CH:20]([OH:21])[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]3=[O:22])=[N:9]2)=[CH:4][CH:3]=1.[N:23]([CH2:26][C:27]([O:29][CH3:30])=[O:28])=[C:24]=[O:25].C(N(CC)CC)C>C(#N)C>[Cl:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([N:12]3[CH:20]([O:21][C:24]([NH:23][CH2:26][C:27]([O:29][CH3:30])=[O:28])=[O:25])[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]3=[O:22])=[N:9]2)=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 2769479Methyl 2-isocyanatoacetate2 回HCID 199004082-(7-Chloro-1,8-naphthyridin-2-yl)-3-hydroxyisoindolin-1-one

生成物 1

HCID 227547422-(7-Chloro-1,8-naphthyridin-2-yl)-3-methoxycarbonylmethylaminocarbonyloxy-isoindolin-1-one収率 57.1%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
20 °C

実験手順

A suspension of 2-(7-chloro-1,8-naphthyridin-2-yl)-3-hydroxy-isoindolin-1-one (3.2 g.), methyl 2-isocyanatoacetate (1.4 g.) and triethylamine (1.2 g.) in acetonitrile (50 cc.) is stirred for 18 hours at a temperature of about 20° C. A further amount of methyl 2-isocyanatoacetate (0.7 g.) is added and stirring is continued for a further 3 hours. The precipitate is filtered off and is dissolved in methylene chloride (35 cc.). Decolourising charcoal (0.5 g.) is added. After filtration, diisopropyl ether (105 cc.) is added to the filtrate. The crystalline precipitate which forms is filtered off, washed with diisopropyl ether (15 cc.) and then dried to give 2-(7-chloro-1,8-naphthyridin-2-yl)-3-methoxycarbonylmethylaminocarbonyloxy-isoindolin-1-one (2.5 g.) melting at 208°-210° C.

後処理

  1. stirringstirring
  2. waitis continued for a further 3 hours
  3. filtrationThe precipitate is filtered off
  4. dissolutionis dissolved in methylene chloride (35 cc.)
  5. additionDecolourising charcoal (0.5 g.) is added
  6. filtrationAfter filtration, diisopropyl ether (105 cc.)
  7. additionis added to the filtrate
  8. filtrationThe crystalline precipitate which forms is filtered off
  9. washwashed with diisopropyl ether (15 cc.)
  10. customdried

出典と根拠

ORDレコード
ord-ee80e857e132454f926ed910dfa83ab2
出典データセット
uspto-grants-1978_12
特許番号
US04131674

反応ノート

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