Hydrochloric Acid → 4'-(5-Aminopyrazin-2-yl)-5'-fluorobiphenyl-2-thiol

HRID 1523844Notes

Reaction equation

HRID 1523844 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]2[C:13]([F:14])=[CH:12][C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[S:21]CCC(OCC)=O)=[CH:10][CH:9]=2)=[N:6][CH:7]=1.C1COCC1.CC([O-])(C)C.[K+].Cl>O>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]2[C:13]([F:14])=[CH:12][C:11]([C:15]3[C:16]([SH:21])=[CH:17][CH:18]=[CH:19][CH:20]=3)=[CH:10][CH:9]=2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 23665647Potassium tert-butoxideHCID 90313441Ethyl 3-(4'-(5-aminopyrazin-2-yl)-5'-fluorobiphenyl-2-ylthio)propanoate

Product 1

HCID 1364991434'-(5-Aminopyrazin-2-yl)-5'-fluorobiphenyl-2-thiolYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution consisting of ethyl 3-(4′-(5-aminopyrazin-2-yl)-5′-fluorobiphenyl-2-ylthio)propanoate (7.7 g, 19.4 mmol) and THF (60 mL) was added t-BuOK (4.3 g, 38.8 mmol) and the mixture stirred for 1 hour at rt. The reaction mixture was poured into water (100 mL) and the system brought to a pH=5-6 with 1 M HCl. The mixture was, extracted with EtOAc (80 mL×3) and the combined extracts dried over Na2SO4, filtered and concentrated to dryness to give 4′-(5-aminopyrazin-2-yl)-5′-fluorobiphenyl-2-thiol (4.6 g, 80%). MS (ESI): mass calcd. for C16H12FN3S, 297.07; m/z found, 298.0 [M+H]+.

Workup

  1. extractionextracted with EtOAc (80 mL×3)
  2. dry with materialthe combined extracts dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-515a09c7e1144729b41599c1f40d4d04
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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