1-Pyrrolidinecarbonyl chloride → HCID 42645356, compound
Reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([CH3:14])=[C:12]([CH3:15])[S:11][C:10]2=[NH:16])=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.[N:26]1([C:31](Cl)=[O:32])[CH2:30][CH2:29][CH2:28][CH2:27]1>C(#N)C>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C:13]([CH3:14])=[C:12]([CH3:15])[S:11]/[C:10]/2=[N:16]\[C:31]([N:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)=[O:32])=[CH:7][CH:8]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
To a suspension of 3-(4-chlorophenyl)-4,5-dimethyl-1,3-thiazol-2(3H)-imine hydrochloride (90 mg, 0.33 mmol, Example 160A) in acetonitrile (2.0 mL) containing diisopropylethylamine (102 mg, 0.79 mmol) was added 1-pyrrolidinecarbonyl chloride (53 mg, 39 mmol). The mixture was heated at 75° C. for 18 hours, then concentrated. The residue was dissolved in dichloromethane (10 mL). The organic layer was washed with dilute aqueous ammonium chloride (5 mL) and water (2×5 mL) and the dichloromethane was removed under reduced pressure. The residue was purified on a Waters Symmetry C8 30×100 mm column (flow rate 40 mL/min, 5-95% gradient of acetonitrile in 0.1% aqueous trifluoroacetic acid) to afford the title product.
Workup
- concentrationconcentrated
- dissolutionThe residue was dissolved in dichloromethane (10 mL)
- washThe organic layer was washed with dilute aqueous ammonium chloride (5 mL) and water (2×5 mL)
- customthe dichloromethane was removed under reduced pressure
- customThe residue was purified on a Waters Symmetry C8 30×100 mm column (flow rate 40 mL/min, 5-95% gradient of acetonitrile in 0.1% aqueous trifluoroacetic acid)
Sources & evidence
- ORD record
- ord-56976db16f2d49a289b9e19046e13345
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08383657B2
Reaction notes
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