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

HRID 424765노트

반응식

HRID 424765 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
82 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-28671ea0d47a4b69986608059fb3ac82
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106073B2

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