Triethylamine → HCID 11271280, compound

HRID 855574Notes

Reaction equation

HRID 855574 reaction equation
Cl[CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]1=[O:13].[CH3:14][C:15]1[S:16][C:17]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH:26]([OH:34])[CH2:27][N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)=[CH:20][C:18]=2[N:19]=1.CCN(CC)CC>CCO>[OH:34][C@@H:26]([CH2:25][O:24][C:21]1[CH:22]=[CH:23][C:17]2[S:16][C:15]([CH3:14])=[N:19][C:18]=2[CH:20]=1)[CH2:27][N:28]1[CH2:29][CH2:30][N:31]([CH:2]2[CH2:6][CH2:5][N:4]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:3]2=[O:13])[CH2:32][CH2:33]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 219116911-(2-Methylbenzothiazol-5-yloxy)-3-piperazin-1-ylpropan-2-olHCID 219355593-Chloro-1-phenylpyrrolidin-2-one

Product 1

HCID 11271280HCID 11271280, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 3-chloro-1-phenylpyrrolidin-2-one (100 mg, 0.51 mmol) in EtOH (10 mL) was added 1-(2-methylbenzothiazol-5-yloxy)-3-piperazin-1-ylpropan-2-ol as prepared in Example 3A (190 mg, 0.62 mmol) and Et3N (0.2 mL, 1.43 mmol). The solution was stirred at 85° C. for 60 hours. Upon cooling, the solution was concentrated to an oil and purified via flash column chromatography to afford 3-{4-[(2R)-2-hydroxy-3-(2-methylbenzothiazol-5-yloxy)propyl]piperazinyl}-1-phenylpyrrolidin-2-one.

Workup

  1. temperatureUpon cooling
  2. concentrationthe solution was concentrated to an oil
  3. custompurified via flash column chromatography

Sources & evidence

ORD record
ord-dd86d7c8da544fdab19674c119f12a77
Source dataset
uspto-grants-2007_08
Patent number
US07262198B2

Reaction notes

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