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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → trans-3-(3-Cyano-phenylcarbamoyl)-4-[3-(5-methyl-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-ylcarbamoyl)-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1524291
ノート
印刷プレビュー

反応式

HRID 1524291 の反応式
CN(C)CCCN=C=NCC.OC1C2N=NNC=2C=CC=1.C(N(CC)C(C)C)(C)C.[C:31]([O:35][C:36]([N:38]1[CH2:42][C@@H:41]([C:43](=[O:53])[NH:44][C:45]2[CH:50]=[CH:49][CH:48]=[C:47]([C:51]#[N:52])[CH:46]=2)[C@H:40]([C:54]2[CH:59]=[CH:58][CH:57]=[C:56]([C:60](O)=[O:61])[CH:55]=2)[CH2:39]1)=[O:37])([CH3:34])([CH3:33])[CH3:32].[CH3:63][N:64]1[CH2:69][CH2:68][C:67]2[N:70]=[C:71]([NH2:73])[S:72][C:66]=2[CH2:65]1>CC(N(C)C)=O.O>[C:31]([O:35][C:36]([N:38]1[CH2:39][C@@H:40]([C:54]2[CH:59]=[CH:58][CH:57]=[C:56]([C:60](=[O:61])[NH:73][C:71]3[S:72][C:66]4[CH2:65][N:64]([CH3:63])[CH2:69][CH2:68][C:67]=4[N:70]=3)[CH:55]=2)[C@H:41]([C:43](=[O:53])[NH:44][C:45]2[CH:50]=[CH:49][CH:48]=[C:47]([C:51]#[N:52])[CH:46]=2)[CH2:42]1)=[O:37])([CH3:33])([CH3:34])[CH3:32]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 23979985-methyl-4H,5H,6H,7H-[1,3]thiazolo[5,4-c]pyridin-2-amineHCID 68089451trans-3-(3-Carboxy-phenyl)-4-(3-cyano-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 178418300HCID 178418300、化合物

生成物 1

HCID 86667843
trans-3-(3-Cyano-phenylcarbamoyl)-4-[3-(5-methyl-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-ylcarbamoyl)-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester
収率 100.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 31374Dimethylacetamide溶媒

実験手順

Add N-(-3-dimethylaminopropyl)-N′-ethylcarbodiimide (0.10 g, 0.52 mmol), followed by hydroxybenzotriazole (0.07 g, 0.52 mmol) and N,N-diisopropylethyl amine (0.18 mL, 1.00 mmol) to a solution of trans-3-(3-carboxy-phenyl)-4-(3-cyano-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.17 g, 0.39 mmol) in dimethylacetamide (5 mL). Stir the mixture at room temperature for 1 h then add 5-methyl-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-ylamine (0.08 g, 0.50 mmol) and heat the mixture to 50° C. with stifling overnight. Cool the reaction to room temperature and dilute with water causing a solid to precipitate from solution. Collect the formed solid by filtration, wash with water and dry on the filter pad to provide 0.23 g (quant.) of trans-3-(3-cyano-phenylcarbamoyl)-4-[3-(5-methyl-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-ylcarbamoyl)-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester as a powder.

後処理

  1. temperatureCool
  2. customthe reaction to room temperature
  3. customto precipitate from solution
  4. customCollect the formed solid
  5. filtrationby filtration
  6. washwash with water
  7. customdry on the filter pad

出典と根拠

ORDレコード
ord-154fc6acd8434939a47474d4b1c4802f
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09079880B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート