Dimethylformamide → 2-Chloro-6-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-N-(2-morpholin-4-ylethyl)pyrimidine-4-carboxamide

HRID 2233912Notes

Reaction equation

HRID 2233912 reaction equation
[Cl:1][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.[N:29]1([CH2:35][CH2:36][NH2:37])[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.CN([CH:41]=[O:42])C>CCOC(C)=O.O>[Cl:1][C:2]1[N:3]=[C:4]([C:41]([NH:37][CH2:36][CH2:35][N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)=[O:42])[CH:5]=[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)[N:7]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 4082852-MorpholinoethylamineHCID 178499026HCID 178499026, compound

Product 1

HCID 866082692-Chloro-6-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-N-(2-morpholin-4-ylethyl)pyrimidine-4-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

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: 380 mg, 0.85 mmol), 2-morpholin-4-ylethanamine (222 mg, 1.70 mmol) and TEA (0.12 ml, 0.85 mmol) in DMF (3 ml) were stirred at 60° C. under nitrogen for 18 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 under vacuum. Purification by reversed-phase HPLC (water/acetonitrile gradient, 5-95%) provided 110 mg of the title compound.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customPurification by reversed-phase HPLC (water/acetonitrile gradient, 5-95%)

Sources & evidence

ORD record
ord-9580e420b73744b2a53663e3c11c197e
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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