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

HRID 424770Notes

Reaction equation

HRID 424770 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][NH:4][CH2:3]1.C(#N)C.Cl[C:11]1[CH:20]=[CH:19][C:18]2[C:17]([C:21]([NH:23][CH2:24][C:25]3([OH:32])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)=[O:22])=[C:16]([Cl:33])[CH:15]=[CH:14][C:13]=2[N:12]=1.C(=O)([O-])[O-].[K+].[K+]>O>[NH2:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:11]2[CH:20]=[CH:19][C:18]3[C:17]([C:21]([NH:23][CH2:24][C:25]4([OH:32])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]4)=[O:22])=[C:16]([Cl:33])[CH:15]=[CH:14][C:13]=3[N:12]=2)[CH2:3]1

Participants

6

Reactant 4

HCID 6342Acetonitrile2×HCID 11430Potassium CarbonateHCID 1519351(3S)-(-)-3-AminopyrrolidineHCID 577339892,6-Dichloro-N-((1-hydroxycycloheptyl)methyl)quinoline-5-carboxamide

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(S)-3 aminopyrrolidine (96 ml) and acetonitrile (300 ml) were charged to a vessel containing 2,6-Dichloro-N-((1-hydroxycycloheptyl)methyl)quinoline-5-carboxamide (300.0 g), potassium carbonate (249.0 g) and acetonitrile (2400 ml). The reaction mixture was heated under refux for 20 hours. Water (6900 ml) was charged at 20° C. to 25° C. The mixture was stirred for 95 minutes and filtered. The filter cake was washed with water (1200 ml) and acetonitrile (1200 ml). The filter cake was dried at 40° C. for 48 hours to provide the title compound as a yellow solid (283 g).

Workup

  1. temperatureThe reaction mixture was heated under refux for 20 hours
  2. filtrationfiltered
  3. washThe filter cake was washed with water (1200 ml) and acetonitrile (1200 ml)
  4. customThe filter cake was dried at 40° C. for 48 hours

Sources & evidence

ORD record
ord-ba6ba7f8c9c04223871c75dc40294536
Source dataset
uspto-grants-2012_01
Patent number
US08106073B2

Reaction notes

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