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Sodium methanethiolate → 3,4-Dichloro-5-methyl-N-{1-[2-(methylthio)pyrimidin-4-yl]piperidin-4-yl}-1H-pyrrole-2-carboxamide

HRID 2234040
Notes
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Reaction equation

HRID 2234040 reaction equation
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:23]=[CH:22][N:21]=[C:20](Cl)[N:19]=2)[CH2:14][CH2:13]1)=[O:10].[CH3:25][S-:26].[Na+]>CN(C=O)C.CCOC(C)=O.O>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([S:26][CH3:25])[N:19]=2)[CH2:14][CH2:13]1)=[O:10]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 4378561Sodium methanethiolateHCID 866083433,4-Dichloro-N-[1-(2-chloropyrimidin-4-yl)piperidin-4-yl]-5-methyl-1H-pyrrole-2-carboxamide

Product 1

HCID 685798923,4-Dichloro-5-methyl-N-{1-[2-(methylthio)pyrimidin-4-yl]piperidin-4-yl}-1H-pyrrole-2-carboxamideYield 97%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent
HCID 6228
Dimethylformamide
Solvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

3,4-Dichloro-N-[1-(2-chloropyrimidin-4-yl)piperidin-4-yl]-5-methyl-1H-pyrrole-2-carboxamide (Example 307, 200 mg, 0.515 mmol) and sodium thiomethoxide (108.2 mg, 1.545 mmol) were combined in DMF (12 ml) and heated at 90° C. for 1 h. The reaction mixture was cooled to room temperature, diluted with EtOAc and water. The phases were separated, and the aqueous phase was extracted three times with EtOAc. The combined organic portions were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give a peach coloured solid (200 mg, 0.499 mmol, 97% yield) that was used without further purification.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted three times with EtOAc
  4. washThe combined organic portions were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1ef28c3748404045a8c39f011a2461df
Source dataset
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07709503B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes