Triethylamine → (7-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-2-oxo-3,4-dihydroquinolin-1(2H)-yl)methyl 4-acetamidobutanoate

HRID 1971034ノート

反応式

HRID 1971034 の反応式
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:29]=[C:28]3[C:23]([CH2:24][CH2:25][C:26](=[O:32])[N:27]3[CH2:30][OH:31])=[CH:22][CH:21]=2)[CH2:11][CH2:10]1.C(N(CC)CC)C.CS(Cl)(=O)=O.[C:45]([NH:48][CH2:49][CH2:50][CH2:51][C:52](O)=[O:53])(=[O:47])[CH3:46]>ClCCl>[C:45]([NH:48][CH2:49][CH2:50][CH2:51][C:52]([O:31][CH2:30][N:27]1[C:28]2[C:23](=[CH:22][CH:21]=[C:20]([O:19][CH2:18][CH2:17][CH2:16][CH2:15][N:12]3[CH2:13][CH2:14][N:9]([C:3]4[CH:4]=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=4[Cl:1])[CH2:10][CH2:11]3)[CH:29]=2)[CH2:24][CH2:25][C:26]1=[O:32])=[O:53])(=[O:47])[CH3:46]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 181894-Acetamidobutyric acidHCID 31297Methanesulfonyl chlorideHCID 58096483N-Hydroxymethyl aripiprazole

生成物 1

HCID 49853670(7-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-2-oxo-3,4-dihydroquinolin-1(2H)-yl)methyl 4-acetamidobutanoate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a suspension of hemiaminal A1 (2.6 g, 5.5 mmol) in dichloromethane (30 mL) was added triethylamine (2.3 mL, 16.4 mmol), followed by addition of methanesulfonyl chloride (0.47 g, 6.0 mmol) over 3 min. The reaction mixture was stirred for 25 min and then N-acetyl-4-aminobutyric acid (1.6 g, 10.1 mmol) added. The reaction mixture was then heated at reflux for 18 h, cooled and washed with sat. NaHCO3 (aq). The organic phase was dried over MgSO4, filtered and evaporated. The residue was further purified on silica eluting with 1:1:0.1 to 1:1:0.2 dichloromethane/ethyl acetate/methanol to give the title compound as an off white solid (1.1 g, 34%).

後処理

  1. temperatureThe reaction mixture was then heated
  2. temperatureat reflux for 18 h
  3. temperaturecooled
  4. washwashed with sat. NaHCO3 (aq)
  5. dry with materialThe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was further purified on silica eluting with 1:1:0.1 to 1:1:0.2 dichloromethane/ethyl acetate/methanol

出典と根拠

ORDレコード
ord-baf279eecaf445b284489dd4fe961118
出典データセット
uspto-grants-2013_04
特許番号
US08431576B2

反応ノート

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