L-Hydroxyproline → HCID 21822966, compound

HRID 553458Notes

Reaction equation

HRID 553458 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH:8][C:9](=[O:12])OC.O[C@H]1C[NH:17][C@H:16]([C:19](O)=O)[CH2:15]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(N)(C)C>[Cu]I.CS(C)=O>[CH:16]([N:17]1[C:2]2[CH:3]=[N:4][CH:5]=[CH:6][C:7]=2[NH:8][C:9]1=[O:12])([CH3:19])[CH3:15]

Participants

7

Reactant 4

HCID 5810L-HydroxyprolineHCID 6363IsopropylamineHCID 62657Potassium Phosphate, TribasicHCID 57924514HCID 57924514, compound

Product 1

HCID 21822966HCID 21822966, compoundYield 142%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

A sealed tube was charged with methyl 3-bromopyridin-4-ylcarbamate (1.76 g, 7.6 mmol.), CuI (290 mg, 1.52 mmol.), trans-4-hydroxy-L-proline (400 mg, 3.04 mmol.) and K3PO4 (3.2 g, 15.2 mmol.), evacuated and backfilled with argon. Isopropylamine (674 mg, 11.4 mmol.) and DMSO (15 mL) were added successively. The reaction mixture was stirred at 70° C. for 12 h and then at 130° C. for 12 h. The reaction mixture filtered and the filtrate was concentrated and purified by prep-HPLC to afford 3-isopropyl-1H-imidazo[4,5-c]pyridin-2(3H)-one (765 mg, 57%).

Workup

  1. customevacuated
  2. waitat 130° C. for 12 h
  3. filtrationThe reaction mixture filtered
  4. concentrationthe filtrate was concentrated
  5. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-67c6249ebc774af9a86179249435ddf8
Source dataset
uspto-grants-2011_11
Patent number
US08048862B2

Reaction notes

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