Morpholine → Methyl 6-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-2-morpholin-4-ylpyrimidine-4-carboxylate

HRID 2233909Notes

Reaction equation

HRID 2233909 reaction equation
Cl[C:2]1[NH:7][C:6]([N:12]2[CH2:17][CH2:16][CH:15]([NH:18][C:19]([C:21]3[NH:22][C:23]([CH3:28])=[C:24]([Cl:27])[C:25]=3[Cl:26])=[O:20])[CH2:14][CH2:13]2)(C(OC)=O)[CH:5]=[CH:4][N:3]=1.[NH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.C[CH2:36][O:37][C:38](C)=[O:39]>CN(C=O)C.O>[Cl:26][C:25]1[C:24]([Cl:27])=[C:23]([CH3:28])[NH:22][C:21]=1[C:19]([NH:18][CH:15]1[CH2:16][CH2:17][N:12]([C:6]2[N:7]=[C:2]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)[N:3]=[C:4]([C:38]([O:37][CH3:36])=[O:39])[CH:5]=2)[CH2:13][CH2:14]1)=[O:20]

Participants

6

Reactant 3

HCID 8083MorpholineHCID 8857Ethyl AcetateHCID 178499026HCID 178499026, compound

Product 1

HCID 68581162Methyl 6-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-2-morpholin-4-ylpyrimidine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 2-chloro-6-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)pyrimidine-4-carboxylate (Example 6, 300 mg, 0.67 mmol), morpholine (58 mg, 0.67 mmol) and TEA (0.09 ml, 0.67 mmol) in DMF (3 ml) were stirred at 60° C. under nitrogen for 4 hours. The mixture was cooled to room temperature and diluted with EtOAc (75 ml) and water (10 ml). The organic layer was separated, dried over Na2SO4, filtered and concentrated in vacuo to yield 320 mg of the title compound. An analytical sample was purified by reversed-phase HPLC (water/acetonitrile gradient, 20-95%).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5d37eafe1d404ba99e72418e6a63b4ec
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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