1,1'-Carbonyldiimidazole → 5-Chloro-3-(4-(2-methyl-4-thiazolyl)-2-thenoyl)-2-oxindole-1-carboxamide

HRID 581093

反応式

HRID 581093 の反応式
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:8]=[C:9]([C:12]([OH:14])=O)[S:10][CH:11]=2)[N:6]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[N:33]([C:37]([NH2:39])=[O:38])[C:32](=[O:40])[CH2:31]2>CN(C)C=O.CN(C1C=CN=CC=1)C>[Cl:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[N:33]([C:37]([NH2:39])=[O:38])[C:32](=[O:40])[CH:31]2[C:12](=[O:14])[C:9]1[S:10][CH:11]=[C:7]([C:5]2[N:6]=[C:2]([CH3:1])[S:3][CH:4]=2)[CH:8]=1

参加物

6

反応物 3

HCID 682631,1'-CarbonyldiimidazoleHCID 98591595-Chloro-2-oxo-2,3-dihydro-1H-indole-1-carboxamideHCID 150073574-(2-Methylthiazol-4-yl)-2-thiophenecarboxylic acid

生成物 1

HCID 98232915-Chloro-3-(4-(2-methyl-4-thiazolyl)-2-thenoyl)-2-oxindole-1-carboxamide

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒2 回

実験手順

The title compound was prepared according to the procedure of Example 55. A 1.25 g (5.55 mmoles) sample of 4-(2-methyl-4-thiazolyl)-2-thiophenecarboxylic acid (prepared as described in Example 18) was converted to the acyl imidazole by reaction with 0.98 g (6.05 mmoles) of 1,1'-carbonyldiimidazole in 15 ml of N,N-dimethylformamide. After complete reaction this solution was transferred to an addition funnel and slowly added 1.06 g (5.04 mmoles) of 5-chloro-2-oxindole-1-carboxamide and 1.66 g (13.59 mmoles) of 4-(N,N-dimethylamino)pyridine in 50 ml of N,N-dimethyl-formamide. Acidic workup followed by filtration and trituration with 2-butanone gave 0.50 g (1.20 mmoles) of title compound as a yellow solid, m.p. 238-241° C.

後処理

  1. customThe title compound was prepared
  2. customAfter complete reaction this solution
  3. customwas transferred to an addition funnel
  4. filtrationAcidic workup followed by filtration and trituration with 2-butanone

出典と根拠

ORDレコード
ord-f238a35d5b55441d94ad73a82029f2f6
出典データセット
uspto-grants-1999_07
特許番号
US05919809

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