Hydrochloric Acid → HCID 58009945, compound

HRID 1969824Notes

Reaction equation

HRID 1969824 reaction equation
Cl.[S:2]([N:12]1[C:16]2=[N:17][CH:18]=[C:19]([C:21]([O:23]C)=[O:22])[N:20]=[C:15]2[CH:14]=[CH:13]1)([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)(=[O:4])=[O:3]>O1CCOCC1>[S:2]([N:12]1[C:16]2=[N:17][CH:18]=[C:19]([C:21]([OH:23])=[O:22])[N:20]=[C:15]2[CH:14]=[CH:13]1)([C:5]1[CH:6]=[CH:7][C:8]([CH3:9])=[CH:10][CH:11]=1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58010044HCID 58010044, compound

Product 1

HCID 58009945HCID 58009945, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

HCl (6 N aqueous, 714 mL) was added to a yellow solution of methyl 5-tosyl-5H-pyrrolo[2,3-b]pyrazine-2-carboxylate (17.8 g, 53.6 mmol) in 1,4-dioxane (715 mL) within a 2 L round bottom flask, and the mixture was heated at about 60° C. for about 16 h. The reaction mixture was cooled to ambient temperature. The organic solvent was removed under reduced pressure and the precipitate was collected, washed with water, and dried to yield 5-tosyl-5H-pyrrolo[2,3-b]pyrazine-2-carboxylic acid (14.4 g, 85%) as a yellow solid: LC/MS (Table 1, Method a) Rt=1.63 min; MS m/z 316 (M−H)−.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. customThe organic solvent was removed under reduced pressure
  3. customthe precipitate was collected
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-c8bdbf1bbc2141d1bbb09448c546c365
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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