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

HRID 424765Notes

Reaction equation

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

Participants

Conditions

Temperature: 82 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-28671ea0d47a4b69986608059fb3ac82
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106073B2

Reaction notes

Loading…