Chloroacetaldehyde → HCID 58654351, compound

HRID 1170544Notes

Reaction equation

HRID 1170544 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl[CH2:8][CH:9]=O.[C:11]([O:15][C:16]([N:18]1[CH2:22][CH2:21][CH:20]([C:23](=[S:25])[NH2:24])[CH:19]1[C:26]1[CH:31]=[C:30]([CH3:32])[N:29]=[C:28]([N:33]2[CH:37]=[CH:36][N:35]=[CH:34]2)[N:27]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12].FC(F)(F)C(OC(=O)C(F)(F)F)=O.N1C=CC=CC=1>COCCOC>[C:11]([O:15][C:16]([N:18]1[CH2:22][CH2:21][CH:20]([C:23]2[S:25][CH:8]=[CH:9][N:24]=2)[CH:19]1[C:26]1[CH:31]=[C:30]([CH3:32])[N:29]=[C:28]([N:33]2[CH:37]=[CH:36][N:35]=[CH:34]2)[N:27]=1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

7

Reactant 5

HCID 33ChloroacetaldehydeHCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 11430Potassium CarbonateHCID 57355453tert-Butyl 3-carbamothioyl-2-[2-(1H-imidazol-1-yl)-6-methylpyrimidin-4-yl]pyrrolidine-1-carboxylate

Product 1

HCID 58654351HCID 58654351, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Potassium carbonate (700 mg, 5.20 mmol) and 2-chloroacetaldehyde (400 mg, 5.20 mmol) were added sequentially to a solution of 2-(2-imidazol-1-yl-6-methyl-pyrimidin-4-yl)-3-thiocarbamoyl-pyrrolidine-1-carboxylic acid tert-butyl ester (400 mg, 1.04 mmol) in DME (10 mL) at rt under an atmosphere of N2. The reaction mixture was stirred at room temperature for 16 h then filtered under vacuum. The filtrate was concentrated and the residue dissolved in DME (10 mL) prior to cooling to 0° C. Trifluoroacetic anhydride (655 mg, 3.12 mmol) and pyridine (575 mg, 7.28 mmol) were added and reaction mixture was stirred at rt for 4 h. The mixture was concentrated and the residue was diluted with DCM (20 mL). The solution was washed with water (2×30 mL), dried over Na2SO4, filtered and concentrated. The crude product was purified using column chromatography (DCM to 9:1 DCM/MeOH) to afford 2-(2-imidazol-1-yl-6-methyl-pyrimidin-4-yl)-3-thiazol-2-yl-pyrrolidine-1-carboxylic acid tert-butyl ester as a yellow oil (200 mg, 50%).

Workup

  1. filtrationthen filtered under vacuum
  2. concentrationThe filtrate was concentrated
  3. dissolutionthe residue dissolved in DME (10 mL)
  4. temperatureto cooling to 0° C
  5. customreaction mixture
  6. stirringwas stirred at rt for 4 h
  7. concentrationThe mixture was concentrated
  8. additionthe residue was diluted with DCM (20 mL)
  9. washThe solution was washed with water (2×30 mL)
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customThe crude product was purified

Sources & evidence

ORD record
ord-801ba7f40ed944e49d1e742db26be1b7
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

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