4-Methylmorpholine → HCID 22285672, compound

HRID 1168088Notes

Reaction equation

HRID 1168088 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([CH2:21][CH:22]2[S:26][C:25](=[O:27])[NH:24][C:23]2=[O:28])[CH:18]=[C:17]([Cl:29])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([O:15][CH3:16])=[C:9]([S:11](Cl)(=[O:13])=[O:12])[CH:10]=1.[CH:30]1([NH2:33])[CH2:32][CH2:31]1.CN1CCOCC1>O1CCCC1>[CH:30]1([NH:33][S:11]([C:9]2[CH:10]=[C:5]([O:4][C:3]3[C:2]([Cl:1])=[CH:20][C:19]([CH2:21][CH:22]4[S:26][C:25](=[O:27])[NH:24][C:23]4=[O:28])=[CH:18][C:17]=3[Cl:29])[CH:6]=[CH:7][C:8]=2[O:15][CH3:16])(=[O:13])=[O:12])[CH2:32][CH2:31]1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 69828CyclopropylamineHCID 22285655HCID 22285655, compound

Product 1

HCID 22285672HCID 22285672, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the title compound of Step E (38 mg, 0.08 mmol) in dry tetrahydrofuran (1 ml) at room temperature was added cyclopropylamine (8.0 mL, 0.12 mmol) and N-methylmorpholine (17 ml, 0.15 mmol). The reaction mixture was stirred at room temperature for two hours, quenched with 1N HCl (15 ml), and extracted with ethyl acetate (3×15 ml). The combined extracts were washed with 1N HCl (2×15 ml), brine (15 ml), dried over sodium sulfate, filtered, and concentrated. The residue was purified by preparative TLC (8% methanol in dichloromethane) to afford the title compound (16 mg, 41% yield). MS (APCl+) Calc: 516.0, Found: 516.9 (M+1).

Workup

  1. customquenched with 1N HCl (15 ml)
  2. extractionextracted with ethyl acetate (3×15 ml)
  3. washThe combined extracts were washed with 1N HCl (2×15 ml), brine (15 ml)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by preparative TLC (8% methanol in dichloromethane)

Sources & evidence

ORD record
ord-80464189b5b3400381c43a2d7d9dfd69
Source dataset
uspto-grants-2003_09
Patent number
US06620830B2

Reaction notes

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