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

HRID 390173노트

반응식

HRID 390173 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f008275bae6041bbba3df741e83643dc
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383629B2

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