4-Methylmorpholine → HCID 68988679, compound
Reaction equation
[Br:1][CH:2]([CH2:6][CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)[C:3](Cl)=[O:4].CN1CCOCC1.[N:19]1[CH:24]=[CH:23][N:22]=[CH:21][C:20]=1[NH2:25]>O1CCCC1>[Br:1][CH:2]([CH2:6][CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)[C:3]([NH:25][C:20]1[CH:21]=[N:22][CH:23]=[CH:24][N:19]=1)=[O:4]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 2-bromo-3-cyclopentyl-propionyl chloride (1.46 g, 6.09 mmol) in tetrahydrofuran (32.1 mL, 0.19M) cooled to 0° C. was treated with N-methylmorpholine (0.66 mL, 6.09 mmol). The reaction mixture was stirred at 0° C. for 5 min. After this time, the reaction was treated with pyrazin-2-ylamine (0.58 g, 6.09 mmol) and allowed to warm to 25° C. The reaction stirred at 25° C. for 2 d. After this time, the reaction mixture was partitioned between water (100 mL) and ethyl acetate (2×150 mL). The organics were dried over sodium sulfate, filtered and concentrated in vacuo. Silica gel column chromatography (AnaLogix, 115 g, 10-50% ethyl acetate/hexanes gradient) afforded 2-bromo-3-cyclopentyl-N-pyrazin-2-yl-propionamide (0.43 g, 24%) as a light brown solid; ES+-HRMS m/e calcd for C12H16N3OBr [M+H+] 298.0550, found 298.0550.
Workup
- temperatureto warm to 25° C
- stirringThe reaction stirred at 25° C. for 2 d
- customAfter this time, the reaction mixture was partitioned between water (100 mL) and ethyl acetate (2×150 mL)
- dry with materialThe organics were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-6364eb04cb1e4a3fa064e0862e68e25d
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08258134B2
Reaction notes
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