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Pyridine → N-{4-[(Dimethylamino)carbonyl]phenyl}-5-[(3,3-dimethylbutanoyl)amino]-1-(2-fluorobenzyl)-1H-indole-2-carboxamide

HRID 1825006
ノート
印刷プレビュー

反応式

HRID 1825006 の反応式
[CH3:1][C:2]([CH3:28])([CH3:27])[CH2:3][C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[F:23])[C:11]([C:24](O)=[O:25])=[CH:10]2)=[O:5].N1C=CC=CC=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:59][C:60]1[CH:70]=[CH:69][C:63]([C:64]([N:66]([CH3:68])[CH3:67])=[O:65])=[CH:62][CH:61]=1>CN(C=O)C.O>[CH3:67][N:66]([CH3:68])[C:64]([C:63]1[CH:69]=[CH:70][C:60]([NH:59][C:24]([C:11]2[N:12]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[F:23])[C:13]3[C:9]([CH:10]=2)=[CH:8][C:7]([NH:6][C:4](=[O:5])[CH2:3][C:2]([CH3:27])([CH3:1])[CH3:28])=[CH:15][CH:14]=3)=[O:25])=[CH:61][CH:62]=1)=[O:65]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 1049PyridineHCID 2355274-Amino-N,N-dimethylbenzamideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 221446405-[(3,3-Dimethylbutanoyl)amino]-1-(2-fluorobenzyl)-1H-indole-2-carboxylic acid

生成物 1

HCID 22144662
N-{4-[(Dimethylamino)carbonyl]phenyl}-5-[(3,3-dimethylbutanoyl)amino]-1-(2-fluorobenzyl)-1H-indole-2-carboxamide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

Under argon, 200 mg (0.43 mmol) of 5-[(3,3-dimethylbutanoyl)amino]-1-(2-fluorobenzyl)-1H-indole-2-carboxylic acid (Example XXXIX) are dissolved in 2 ml of DMF, and 4 ml of pyridine are added. 489.2 mg (1.29 mmol) of HATU are added to this solution, 140.8 mg (0.86 mmol) of 4-amino-N,N-dimethylbenzamide are then slowly added dropwise and the reaction mixture is stirred at RT overnight. For work-up, water is added and the mixture is extracted repeatedly with ethyl acetate. The combined organic phases are dried over sodium sulphate and filtered, and the solvent is removed under reduced pressure. The residue is purified by preparative HPLC. This gives 47.4 mg (15% of theory) of product.

後処理

  1. additionare then slowly added dropwise
  2. extractionthe mixture is extracted repeatedly with ethyl acetate
  3. dry with materialThe combined organic phases are dried over sodium sulphate
  4. filtrationfiltered
  5. customthe solvent is removed under reduced pressure
  6. customThe residue is purified by preparative HPLC

出典と根拠

ORDレコード
ord-a9602eb638114291961e5a6205cf1268
出典データセット
uspto-grants-2006_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07045544B2

反応ノート

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