Acetonitrile → 2-[(3S)-3-Aminopyrrolidin-1-yl]-6-chloro-N-[(1-hydroxycycloheptyl)methyl]-quinoline-5-carboxamide

HRID 424765ノート

反応式

HRID 424765 の反応式
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:8]([C:12]([NH:14][CH2:15][C:16]3([OH:23])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:13])=[C:7]([Cl:24])[CH:6]=[CH:5][C:4]=2[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[NH2:31][C@H:32]1[CH2:36][CH2:35][NH:34][CH2:33]1.C(#N)C>O>[NH2:31][C@H:32]1[CH2:36][CH2:35][N:34]([C:2]2[CH:11]=[CH:10][C:9]3[C:8]([C:12]([NH:14][CH2:15][C:16]4([OH:23])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]4)=[O:13])=[C:7]([Cl:24])[CH:6]=[CH:5][C:4]=3[N:3]=2)[CH2:33]1

参加物

6

反応物 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 1519351(3S)-(-)-3-AminopyrrolidineHCID 577339892,6-Dichloro-N-((1-hydroxycycloheptyl)methyl)quinoline-5-carboxamide

生成物 1

HCID 577339902-[(3S)-3-Aminopyrrolidin-1-yl]-6-chloro-N-[(1-hydroxycycloheptyl)methyl]-quinoline-5-carboxamide

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
82 °C

実験手順

A mixture of 2,6-dichloro-N-((1-hydroxycycloheptyl)methyl)quinoline-5-carboxamide (100 g), potassium carbonate (83 g), (S)-3-aminopyrrolidine (Alfa Aesar, 99% ee) (41 ml) and acetonitrile (1 L) were heated with stirring at 82° C. under a nitrogen atmosphere for 8 hours. The mixture was then allowed to cool to room temperature, poured into water (3.3 L) and the mixture was stirred for 1 hour before being filtered and washed with water (2×300 ml), acetonitrile (200 ml) and dried in vacuo to afford the subtitle product as a pale yellow solid (94.0 g).

後処理

  1. temperaturewere heated
  2. temperatureto cool to room temperature
  3. stirringthe mixture was stirred for 1 hour
  4. filtrationbefore being filtered
  5. washwashed with water (2×300 ml), acetonitrile (200 ml)
  6. customdried in vacuo

出典と根拠

ORDレコード
ord-28671ea0d47a4b69986608059fb3ac82
出典データセット
uspto-grants-2012_01
特許番号
US08106073B2

反応ノート

読み込み中…