Dimethylamine, hydrochloride → (E)-N,N,1-trimethyl-2-oxo-1'-(3-(2-(trifluoromethyl)phenyl)acryloyl)spiro[indoline-3,4'-piperidine]-5-carboxamide

HRID 390169ノート

反応式

HRID 390169 の反応式
[CH3:1][N:2]1[C:29]2[C:24](=[CH:25][C:26]([C:30](O)=[O:31])=[CH:27][CH:28]=2)[C:4]2([CH2:9][CH2:8][N:7]([C:10](=[O:23])/[CH:11]=[CH:12]/[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]([F:22])([F:21])[F:20])[CH2:6][CH2:5]2)[C:3]1=[O:33].C[CH2:35][N:36]=[C:37]=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.N(C)C.Cl>C(Cl)Cl>[CH3:35][N:36]([CH3:37])[C:30]([C:26]1[CH:25]=[C:24]2[C:4]3([CH2:5][CH2:6][N:7]([C:10](=[O:23])/[CH:11]=[CH:12]/[C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[C:19]([F:22])([F:21])[F:20])[CH2:8][CH2:9]3)[C:3](=[O:33])[N:2]([CH3:1])[C:29]2=[CH:28][CH:27]=1)=[O:31]

参加物

7

反応物 5

HCID 10473Dimethylamine, hydrochlorideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 58295682(E)-1-methyl-2-oxo-1'-(3-(2-(trifluoromethyl)phenyl)acryloyl)spiro[indoline-3,4'-piperidine]-5-carboxylic acid

生成物 1

HCID 58295794(E)-N,N,1-trimethyl-2-oxo-1'-(3-(2-(trifluoromethyl)phenyl)acryloyl)spiro[indoline-3,4'-piperidine]-5-carboxamide収率 14%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a mixture of (E)-1-methyl-2-oxo-1′-(3-(2-(trifluoromethyl)phenyl)acryloyl)spiro[indoline-3,4′-piperidine]-5-carboxylic acid (20 mg, 0.508 mmol), EDCI (18 mg, 0.088 mmol), HOBt (12 mg, 0.088 mmol), and DIEA (60 mg, 0.44 mmol) in CH2Cl2 was added NHMe2.HCl (16 mg, 0.176 mmol) at 0° C. The mixture was stirred at rt overnight. The mixture was concentrated to give the crude product, which was purified by preparative TLC to give (E)-N,N,1-trimethyl-2-oxo-1′-(3-(2-(trifluoromethyl)phenyl)acryloyl)spiro[indoline-3,4′-piperidine]-5-carboxamide (6 mg, 14%). 1H NMR (400 MHz, CDCl3): δ=3.05 (m, 6H), 3.25 (m, 3H), 3.60-3.75 (m, 2H), 3.95 (m, 2H), 4.15 (m, 1H), 4.35 (m, 1H), 6.85 (m, 1H), 7.35 (m, 1H), 7.45 (m, 2H), 7.55 (m, 1H) 7.70 (m, 2H), 8.00 (m, 1H).

後処理

  1. concentrationThe mixture was concentrated
  2. customto give the crude product, which
  3. customwas purified by preparative TLC

出典と根拠

ORDレコード
ord-450488b86c8148f7b658a8292c3e93b6
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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