4-Methylmorpholine → HCID 67775663, compound

HRID 1808815Notes

Reaction equation

HRID 1808815 reaction equation
[CH3:1][NH:2][C@@H:3]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:4][N:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1.CN1CCOCC1.[Cl:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][C:30]=1[Cl:31])[C:25](Cl)=[O:26]>CN(C=O)C>[Cl:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][C:30]=1[Cl:31])[C:25]([N:2]([C@@H:3]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:4][N:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1)[CH3:1])=[O:26]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 76403Benzoyl chloride, 3,4-dichloro-HCID 7154286HCID 7154286, compound

Product 1

HCID 67775663HCID 67775663, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (S)—N,3,3-trimethyl-1-(pyrrolidin-1-yl)butan-2-amine (Compound M1) (75 mg, 0.41 mmol) in DMF (1.5 mL) was NMM (0.049 mL, 0.45 mmol) and 3,4-dichlorobenzoyl chloride (0.074 mL, 0.53 mmol) added. The resultant mixture was stirred at rt overnight. The mixture was concentrated and the residue dissolved in DCM (5 mL). The organic phase was 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 (109 mg, 75%). Mixture of rotamers: 1H NMR (400 MHz, DMSO-d6) δ 0.97, 1.35-1.99, 2.07-2.43, 2.52-2.73, 2.93-3.18, 4.57, 6.86-7.18, 7.18-7.37, 7.37-7.61, 7.61-7.88. Total no of protons: 26. HRMS (M+H)+: calculated 357.1500. found 357.1470.

Workup

  1. additionadded
  2. concentrationThe mixture was concentrated
  3. dissolutionthe residue dissolved in DCM (5 mL)
  4. washThe organic phase was washed with NaHCO3 (saturated, 5 mL)
  5. filtrationfiltered through a phase separator
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-40a0045c7e9945fcb1bcc7a38fbebdf4
Source dataset
uspto-grants-2013_01
Patent number
US08361998B2

Reaction notes

Loading…