Dimethyl Sulfoxide → HCID 86616879, compound

HRID 606059Notes

Reaction equation

HRID 606059 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([O:13][CH2:14][C:15]1[N:16]([CH2:29][CH2:30][OH:31])[C:17]2[C:22]([CH3:23])=[C:21]([CH3:24])[N:20]3[N:25]=[N:26][N:27]=[C:19]3[C:18]=2[N:28]=1)[CH3:12].C(N(CC)CC)C>ClCCl>[CH2:11]([O:13][CH2:14][C:15]1[N:16]([CH2:29][CH:30]=[O:31])[C:17]2[C:22]([CH3:23])=[C:21]([CH3:24])[N:20]3[N:25]=[N:26][N:27]=[C:19]3[C:18]=2[N:28]=1)[CH3:12]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 21913508HCID 21913508, compound

Product 1

HCID 86616879HCID 86616879, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To dichloromethane (10 mL) at −78° C. was added dimethylsulfoxide (0.37 mL, 5.17 mmol) and oxalyl chloride (0.33 mL, 3.79 mmol). After several minutes, a solution of 2-[8-(ethoxymethyl)-5,6-dimethyl-7H-imidazo[4,5-c]tetraazolo[1,5-a]pyridin-7-yl]ethanol (prepared as described in U.S. Pat. No. 6,797,718, 1.00 g, 3.44 mmol) in dichloromethane (40 mL) was added dropwise followed by triethylamine (1.5 mL, 10.3 mmol). The mixture was allowed to warm to room temperature and more dichloromethane (80 mL) was added. The solution was transferred to a separatory funnel and washed with saturated aqueous potassium carbonate, water, and brine. The aqueous layers were combined and back-extracted with dichloromethane. The organic phases were combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure to yield the product [8-(ethoxymethyl)-5,6-dimethyl-7H-imidazo[4,5-c]tetraazolo[1,5-a]pyridin-7-yl]acetaldehyde as a tan solid (0.86 g).

Workup

  1. waitAfter several minutes
  2. customThe solution was transferred to a separatory funnel
  3. washwashed with saturated aqueous potassium carbonate, water, and brine
  4. extractionback-extracted with dichloromethane
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2aa937961a14404e8a4e86f6f504c78c
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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