1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 7-Benzyl-3-chloro-4-(3,4-dimethoxyphenyl)-5,6,7,8-tetrahydro-2-(1,2,4-triazol-1-ylacetylaminomethyl)thieno[2,3-b:5,4-c']dipyridine

HRID 1003228

反応式

HRID 1003228 の反応式
C1C=CC2N(O)N=NC=2C=1.C(N=C=NCCCN(C)C)C.[NH2:22][CH2:23][C:24]1[N:29]=[C:28]2[S:30][C:31]3[CH2:32][N:33]([CH2:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[CH2:34][CH2:35][C:36]=3[C:27]2=[C:26]([C:44]2[CH:49]=[CH:48][C:47]([O:50][CH3:51])=[C:46]([O:52][CH3:53])[CH:45]=2)[C:25]=1[Cl:54].[N:55]1([CH2:60][C:61](O)=[O:62])[CH:59]=[N:58][CH:57]=[N:56]1>O.CN(C)C=O>[CH2:37]([N:33]1[CH2:34][CH2:35][C:36]2[C:27]3[C:28]([S:30][C:31]=2[CH2:32]1)=[N:29][C:24]([CH2:23][NH:22][C:61](=[O:62])[CH2:60][N:55]1[CH:59]=[N:58][CH:57]=[N:56]1)=[C:25]([Cl:54])[C:26]=3[C:44]1[CH:49]=[CH:48][C:47]([O:50][CH3:51])=[C:46]([O:52][CH3:53])[CH:45]=1)[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

参加物

7

反応物 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 18101801,2,4-Triazole-1-acetic acidHCID 120436212-Aminomethyl-7-benzyl-3-chloro-4-(3,4-dimethoxyphenyl)-5,6,7,8-tetrahydrothieno[2,3-b:5,4-c']dipyridine

生成物 1

HCID 541666527-Benzyl-3-chloro-4-(3,4-dimethoxyphenyl)-5,6,7,8-tetrahydro-2-(1,2,4-triazol-1-ylacetylaminomethyl)thieno[2,3-b:5,4-c']dipyridine収率 50%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

N-hydroxybenotriazole (HOBt) (0.427 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (WSC) (0.535 g) were added to an ice-cooled mixture of the compound (1.0 g) obtained in Example 18B, (1,2,4-triazol-1-yl)acetic acid (0.325 g) and N,N-dimethylformamide (DMF) (20 ml), the mixture was stirred at room temperature for 8 hours, poured over water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-methanol (20:1, v/v) to yield 7-benzyl-3-chloro-4-(3,4-dimethoxyphenyl)-5,6,7,8-tetrahydro-2-(1,2,4-triazol-1-ylacetylaminomethyl)thieno[2,3-b:5,4-c']dipyridine (0.55 g, 50%), which was then recrystallized from ethyl acetate-hexane to yield a colorless powder having a melting point of 101 to 102° C.

後処理

  1. temperaturecooled
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. washeluted with ethyl acetate-methanol (20:1

出典と根拠

ORDレコード
ord-6b35f1c72a474965852e01759a6f0839
出典データセット
uspto-grants-2000_04
特許番号
US06046189

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