Hydrochloric Acid → 4-({4-[(2R)-2-hydroxy-3-(2-methylbenzothiazol-5-yloxy)propyl]piperazinyl}methyl)-1-(4-fluorophenyl)pyrrolidin-2-one

HRID 271238Notes

Reaction equation

HRID 271238 reaction equation
Br[CH2:2][CH:3]1[CH2:7][N:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[C:5](=[O:15])[CH2:4]1.[CH3:16][C:17]1[S:18][C:19]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][C@H:28]([OH:36])[CH2:29][N:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)=[CH:22][C:20]=2[N:21]=1.Cl.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[OH:36][C@@H:28]([CH2:27][O:26][C:23]1[CH:24]=[CH:25][C:19]2[S:18][C:17]([CH3:16])=[N:21][C:20]=2[CH:22]=1)[CH2:29][N:30]1[CH2:31][CH2:32][N:33]([CH2:2][CH:3]2[CH2:7][N:6]([C:8]3[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=3)[C:5](=[O:15])[CH2:4]2)[CH2:34][CH2:35]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 219354874-(Bromomethyl)-1-(4-fluorophenyl)pyrrolidin-2-oneHCID 29943216(2R)-1-(2-methylbenzothiazol-5-yloxy)-3-piperazinylpropan-2-ol

Product 1

HCID 113525054-({4-[(2R)-2-hydroxy-3-(2-methylbenzothiazol-5-yloxy)propyl]piperazinyl}methyl)-1-(4-fluorophenyl)pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(bromomethyl)-1-(4-fluorophenyl)pyrrolidin-2-one (0.04 g, 0.15 mmol), (2R)-3-(2-methylbenzothiazol-5-yloxy)-1-piperazinylpropan-2-ol 2×HCl (0.09 g, 0.24 mmol), and potassium carbonate (0.150 g, 1.15 mmol) in N,N′dimethylformamide (2 ml) was heated to 70° C. for 16 hours. The solution was filtered and the filtrate concentrated. The residue was purified using preparative chromatography (15:1 DCM:MeOH) to yield 4-({4-[(2R)-2-hydroxy-3-(2-methylbenzothiazol-5-yloxy)propyl]piperazinyl}methyl)-1-(4-fluorophenyl)pyrrolidin-2-one (M+1=498.99).

Workup

  1. filtrationThe solution was filtered
  2. concentrationthe filtrate concentrated
  3. customThe residue was purified

Sources & evidence

ORD record
ord-a4b51a368e90458a9e842aaf925ebcb2
Source dataset
uspto-grants-2008_11
Patent number
US07452889B2

Reaction notes

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