1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (E)-6-(3-(3-acetylazetidin-1-yl)-3-oxoprop-1-enyl)-1'-methyl-1H-spiro[[1,8]naphthyridine-3,4'-piperidin]-2(4H)-one

HRID 83078ノート

反応式

HRID 83078 の反応式
Cl.[NH:2]1[CH2:5][CH:4]([C:6](=[O:8])[CH3:7])[CH2:3]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.Cl.[CH3:40][N:41]1[CH2:46][CH2:45][C:44]2([CH2:55][C:54]3[C:49](=[N:50][CH:51]=[C:52](/[CH:56]=[CH:57]/[C:58](O)=[O:59])[CH:53]=3)[NH:48][C:47]2=[O:61])[CH2:43][CH2:42]1>CN(C)C=O>[C:6]([CH:4]1[CH2:5][N:2]([C:58](=[O:59])/[CH:57]=[CH:56]/[C:52]2[CH:53]=[C:54]3[C:49](=[N:50][CH:51]=2)[NH:48][C:47](=[O:61])[C:44]2([CH2:45][CH2:46][N:41]([CH3:40])[CH2:42][CH2:43]2)[CH2:55]3)[CH2:3]1)(=[O:8])[CH3:7]

参加物

7

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 67154626HCID 67154626、化合物HCID 67154659HCID 67154659、化合物

生成物 1

HCID 68338069(E)-6-(3-(3-acetylazetidin-1-yl)-3-oxoprop-1-enyl)-1'-methyl-1H-spiro[[1,8]naphthyridine-3,4'-piperidin]-2(4H)-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

1-(Azetidin-3-yl)ethanone hydrochloride (110 mg, 0.8 mmol), EDCI (153 mg, 0.8 mmol), HOBt (108 mg, 0.8 mmol) and diisopropylethylamine (700 μL, 4.0 mmol) were successively added to a solution of (E)-3-(1′-methyl-2-oxo-2,4-dihydro-1H-spiro[[1,8]naphthyridine-3,4′-piperidine]-6-yl)acrylic acid hydrochloride (136 mg, 0.4 mmol) in dimethylformamide (15 mL) at room temperature. The reaction mixture was stirred overnight. After concentration to dryness, the residue was purified by chromatography on silica gel using dichloromethane/methanol/ammoniac (9:1:0.1) as eluent. Precipitation in a mixture DCM/pentane allowed isolation of the title product as a yellow solid (44.6 mg, 29%).

後処理

  1. concentrationAfter concentration to dryness
  2. customthe residue was purified by chromatography on silica gel
  3. customPrecipitation in a mixture DCM/pentane allowed isolation of the title product as a yellow solid (44.6 mg, 29%)

出典と根拠

ORDレコード
ord-c6380f37b18c4075aa6a23b497942a03
出典データセット
uspto-grants-2014_09
特許番号
US08846711B2

反応ノート

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