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4-Methylmorpholine → 6-chloro-N5-(1-cyanocyclopropyl)-N2-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2,5-dicarboxamide

HRID 514267
ノート
印刷プレビュー

反応式

HRID 514267 の反応式
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11](=[O:28])[NH:12][CH:13]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=3)[C:14]([F:17])([F:16])[F:15])[NH:8]2)=[CH:4][C:3]=1[C:29]([OH:31])=O.Cl.[NH2:33][C:34]1([C:37]#[N:38])[CH2:36][CH2:35]1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([NH:12][CH:13]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:26])([F:27])[F:25])[CH:19]=3)[C:14]([F:16])([F:17])[F:15])=[O:28])[NH:8]2)=[CH:4][C:3]=1[C:29]([NH:33][C:34]1([C:37]#[N:38])[CH2:36][CH2:35]1)=[O:31]
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 79724-MethylmorpholineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 145863631-Amino-1-cyclopropanecarbonitrile hydrochlorideHCID 867139846-chloro-2-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1H-indole-5-carboxylic acid

生成物 1

HCID 86713985
6-chloro-N5-(1-cyanocyclopropyl)-N2-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2,5-dicarboxamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

6-Chloro-2-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1H-indole-5-carboxylic acid (2.74 g, 5.07 mmol, 86% pure) was dissolved in N,N-dimethylformamide (14 ml), and 1-aminocyclopropanecarbonitrile hydrochloride (0.78 g, 6.59 mmol), N-[(1H-benzotriazol-1-yloxy)(dimethylamino)methylene]-N-methylmethanaminium hexafluorophosphate (2.12 g, 5.07 mmol) and 4-methylmorpholine (1.54 g, 15.2 mmol) were added. The reaction mixture was stirred at room temperature for 16 h and then ethyl acetate was added. The organic phase was washed with hydrochloric acid (1 mol/l) and the aqueous phase was once again extracted with ethyl acetate. The combined organic phases were washed with saturated sodium chloride solution and the portion which was insoluble in both phases was filtered off. The filtercake is triturated with boiling ethyl acetate (15 ml) and the precipitate is washed with warm ethyl acetate. This leaves 2.01 g (74% of theory) of 6-chloro-N5-(1-cyanocyclopropyl)-N2-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2,5-dicarboxamide.

後処理

  1. washThe organic phase was washed with hydrochloric acid (1 mol/l)
  2. extractionthe aqueous phase was once again extracted with ethyl acetate
  3. washThe combined organic phases were washed with saturated sodium chloride solution
  4. filtrationwas filtered off
  5. customThe filtercake is triturated with boiling ethyl acetate (15 ml)
  6. washthe precipitate is washed with warm ethyl acetate

出典と根拠

ORDレコード
ord-b7f3634c7b3c409c912da625c180f480
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09107411B2

反応ノート

読み込み中…

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