Pyridine → (E)-1-methyl-2-oxo-1'-(3-(2-(trifluoromethyl) phenyl)acryloyl)spiro[indoline-3,4'-piperidine]-5-carbonitrile

HRID 390173ノート

反応式

HRID 390173 の反応式
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH3:14][N:15]1[C:42]2[C:37](=[CH:38][C:39]([C:43]([NH2:45])=O)=[CH:40][CH:41]=2)[C:17]2([CH2:22][CH2:21][N:20]([C:23](=[O:36])/[CH:24]=[CH:25]/[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]([F:35])([F:34])[F:33])[CH2:19][CH2:18]2)[C:16]1=[O:46].N1C=CC=CC=1>O1CCOCC1.O>[CH3:14][N:15]1[C:42]2[C:37](=[CH:38][C:39]([C:43]#[N:45])=[CH:40][CH:41]=2)[C:17]2([CH2:22][CH2:21][N:20]([C:23](=[O:36])/[CH:24]=[CH:25]/[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]([F:35])([F:33])[F:34])[CH2:19][CH2:18]2)[C:16]1=[O:46]

参加物

6

反応物 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 58295665(E)-1-methyl-2-oxo-1'-(3-(2-(trifluoromethyl)phenyl)acryloyl)spiro[indoline-3,4'-piperidine]-5-carboxamide

生成物 1

HCID 58295783(E)-1-methyl-2-oxo-1'-(3-(2-(trifluoromethyl) phenyl)acryloyl)spiro[indoline-3,4'-piperidine]-5-carbonitrile

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

A solution of trifluoroacetic anhydride (34 mg, 0.157 mmol) in dioxane (4 mL) was added dropwise to a stirred, ice-cooled solution of (E)-1-methyl-2-oxo-1′-(3-(2-(trifluoromethyl)phenyl)acryloyl)spiro[indoline-3,4′-piperidine]-5-carboxamide (60 mg, 0.131 mmol) and pyridine (60 mg, 0.262 mmol). The reaction mixture was stirred at rt overnight. The mixture was diluted with water and extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated to afford the crude product. After purification by preparative HPLC, (E)-1-methyl-2-oxo-1′-(3-(2-(trifluoromethyl) phenyl)acryloyl)spiro[indoline-3,4′-piperidine]-5-carbonitrile was obtained (2.04 mg, 4%). 1H NMR: (400 MHz, CDCl3): δ=1.85 (m, 4H), 3.20 (m, 3H), 3.80-3.90 (m, 2H), 4.10 (m, 1H), 4.35 (m, 1H), 6.75 (m, 1H), 6.85 (m, 1H), 7.40 (m, 2H), 7.50 (m, 1H), 7.55 (m, 1H) 7.65 (m, 2H), 7.90 (m, 1H).

後処理

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customto afford the crude product
  5. customAfter purification by preparative HPLC

出典と根拠

ORDレコード
ord-f008275bae6041bbba3df741e83643dc
出典データセット
uspto-grants-2013_02
特許番号
US08383629B2

反応ノート

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