4-Methylmorpholine → HCID 67773250, compound

HRID 1808833Notes

Reaction equation

HRID 1808833 reaction equation
[CH3:1][NH:2][C@@H:3]([CH2:10][CH3:11])[CH2:4][N:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1.CN1CCOCC1.[Br:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1>C(Cl)Cl>[Br:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([N:2]([CH3:1])[C@@H:3]([CH2:10][CH3:11])[CH2:4][N:5]2[CH2:9][CH2:8][CH2:7][CH2:6]2)=[O:25])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 685154-Bromobenzoyl chlorideHCID 67773929HCID 67773929, compound

Product 1

HCID 67773250HCID 67773250, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (S)—N-methyl-1-(pyrrolidin-1-yl)butan-2-amine (Compound M5) (75 mg, 0.48 mmol) in DCM (1.5 mL) was NMM (0.058 mL, 0.53 mmol) and 4-bromobenzoyl chloride (137 mg, 0.62 mmol) added. The resultant mixture was stirred at rt overnight. The mixture was diluted with DCM (5 mL), washed with NaHCO3 (saturated, 5 mL), filtered through a phase separator and concentrated under reduced pressure. The residue was purified by preparative HPLC to give the title compound (100 mg, 62%). Mixture of rotamers: 1H NMR (400 MHz, CD3OD) δ 0.92, 1.33-1.66, 1.66-1.97, 2.55, 2.94, 3.64, 4.70-4.83, 7.21-7.49, 7.49-7.76. Ratio major:minor:3:2. Total no of protons: 23.

Workup

  1. additionadded
  2. washwashed with NaHCO3 (saturated, 5 mL)
  3. filtrationfiltered through a phase separator
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-14e66db4c5b44e3e8d600330f438f62b
Source dataset
uspto-grants-2013_01
Patent number
US08361998B2

Reaction notes

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