Hydrochloric Acid → HCID 67367203, compound

HRID 1910965Notes

Reaction equation

HRID 1910965 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:17](=[O:22])C(Cl)(Cl)Cl)[N:5]([CH2:7][C:8]([C:10]2[CH:15]=[N:14][C:13]([CH3:16])=[CH:12][N:11]=2)=[O:9])[CH:6]=1.[OH-:23].[Na+].Cl.[CH3:26]O>O>[Br:1][C:2]1[CH:3]=[C:4]([C:17]([O:22][CH3:26])=[O:23])[N:5]([CH2:7][C:8]([C:10]2[CH:15]=[N:14][C:13]([CH3:16])=[CH:12][N:11]=2)=[O:9])[CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 67368547HCID 67368547, compound

Product 1

HCID 67367203HCID 67367203, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1-{4-bromo-1-[2-(5-methylpyrazin-2-yl)-2-oxoethyl]-1H-pyrrol-2-yl}-2,2,2-trichloroethanone (157 mg, 0.37 mmol) in methanol (7 mL) was treated with sodium hydroxide (15 mg, 0.37 mmol) in water (0.4 mL) at 0° C. and the mixture stirred at room temperature. After one hour the reaction was complete (monitored by LCMS). The mixture was acidified with a aqueous solution of HCl (1 M) and then extracted with CH2Cl2 (3 times). The organic were then dried (Na2SO4), filtrated and concentrated in vacuo to give methyl 4-bromo-1-[2-(5-methylpyrazin-2-yl)-2-oxoethyl]-1H-pyrrole-2-carboxylate (140 mg). The crude was used in the next step without purification. 1H-NMR (400 MHz, CDCl3): δ 2.69 (s, 3H), 3.71 (s, 3H), 5.86 (s, 2H), 6.83 (d, 1H, 1.9 Hz), 7.01 (d, 1H, J 1.9 Hz), 8.53 (s, 1H), 9.13 (s, 1H).

Workup

  1. extractionextracted with CH2Cl2 (3 times)
  2. dry with materialThe organic were then dried (Na2SO4)
  3. filtrationfiltrated
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-72e9b5a97b5f489487b14453df71a4b1
Source dataset
uspto-grants-2013_12
Patent number
US08604034B2

Reaction notes

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