Hydrochloric Acid → HCID 67125632, compound

HRID 1184862Notes

Reaction equation

HRID 1184862 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][C:3]=1[NH:12][C:13]([C:15]1[S:23][C:18]2=[N:19][CH:20]=[CH:21][N:22]=[C:17]2[CH:16]=1)=[O:14].Cl>C(O)C>[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[NH:12][C:13]([C:15]1[S:23][C:18]2=[N:19][CH:20]=[CH:21][N:22]=[C:17]2[CH:16]=1)=[O:14]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67125591HCID 67125591, compound

Product 1

HCID 67125632HCID 67125632, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl 4-methyl-3-(thieno[2,3-b]pyrazine-6-carboxamido)benzoate 49 (480 mg, 1.466 mmol) in ethanol (30 mL) was added 2NaOH (7.33 mL, 14.66 mmol). The mixture was stirred overnight at rt. The mixture was acidified with 2N HCl solution and cooled on ice. the resulting precipitation was collected to give 4-methyl-3-(thieno[2,3-b]pyrazine-6-carboxamido)benzoic acid 50 (310 mg, 67%). NMR (400 MHz, DMSO-d6) 2.36 (s, 3H), 7.46 (d, J=7.8 Hz, 1H), 7.79 (dd, J=7.8 Hz and 1.6 Hz, 1H), 7.96 (d, J=1.6 Hz, 1H), 8.54 (s, 1H), 8.77 (d, J=2.3 Hz, 1H), 8.89 (d, J=2.3 Hz, 1H), 10.57 (s, 1H), 13.01 (br s, 1H). (m/z)=314 (M+H)+.

Workup

  1. temperaturecooled on ice
  2. customthe resulting precipitation
  3. customwas collected

Sources & evidence

ORD record
ord-732a195fdaf343a08df19d396ded592d
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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