Hydrochloric Acid → HCID 67125637, compound

HRID 1184923Notes

Reaction equation

HRID 1184923 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][N:9]=2)[S:4][C:3]=1[C:11]([NH:13][C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][C:23]=1[CH3:24])[C:17]([O:19]C)=[O:18])=[O:12].Cl>C1COCC1.[OH-].[Na+].O>[NH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][N:9]=2)[S:4][C:3]=1[C:11]([NH:13][C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][C:23]=1[CH3:24])[C:17]([OH:19])=[O:18])=[O:12]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 67125579HCID 67125579, compound

Product 1

HCID 67125637HCID 67125637, compoundYield 100.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of methyl 3-(7-aminothieno[2,3-b]pyrazine-6-carboxamido)-4-methylbenzoate 108 (0.803 mmol, 275 mg) in THF (10 mL) and 2N NaOH (10 mL) stirred for 4 h. The red solution was diluted with water, acidified with 2N HCl solution pH 5-6 and extracted with ethyl acetate. The combined organic layers were washed with brine, dried and evaporated to give 3-(7-aminothieno[2,3-b]pyrazine-6-carboxamido)-4-methylbenzoic acid 109 (264 mg, 100%). NMR (400 MHz, DMSO-d6) 2.31 (s, 3H), 7.08 (s, 2H), 7.41 (d, J=8.2 Hz, 1H), 7.75 (dd, J=7.8 Hz and 1.6 Hz, 1H), 7.93 (d, J=1.2 Hz), 8.78 (d, J=2.3 Hz, 1H), 8.79 (d, J=2.3 Hz, 1H), 9.53 (s, 1H), 12.91 (br s, 1H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-c2466327741f46a586ccc74dc2a199a8
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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