Triethylamine → HCID 57637319, compound

HRID 2078742Notes

Reaction equation

HRID 2078742 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]=[C:14]([CH2:16][OH:17])[S:15][C:11]=2[C:10]([I:18])=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>ClCCl>[C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]=[C:14]([CH2:16][O:17][S:27]([CH3:26])(=[O:29])=[O:28])[S:15][C:11]=2[C:10]([I:18])=[N:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57637312HCID 57637312, compound2×

Product 1

HCID 57637319HCID 57637319, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To 5-hydroxymethyl-3-iodo-thieno[3,2-c]pyrazole-1-carboxylic acid tert-butyl ester [220 mg, 0.58 mmol, Intermediate (80)] in dichloromethane (5 mL) were added triethylamine (85 μL, 0.67 mmol), and methane sulfonyl chloride (50 μL, 0.67 mmol). The mixture was stirred at 0° C. for 15 minutes then at room temperature for 30 minutes. The solution was washed with saturated sodium bicarbonate. The organic layer was dried over magnesium sulfate and concentrated to afford 3-iodo-5-methanesulfonyloxymethyl-thieno[3,2-c]pyrazole-1-carboxylic acid tert-butyl ester [220 mg, 79%, Intermediate (81)] as a white foam. LC/MS: 458.97 (M+H), RT=3.39 minutes.

Workup

  1. waitat room temperature for 30 minutes
  2. washThe solution was washed with saturated sodium bicarbonate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ddf472a8bb1f4eeb97548b5121ed26e6
Source dataset
uspto-grants-2011_04
Patent number
US07928231B2

Reaction notes

Loading…