Water → HCID 86690321, compound

HRID 1428671Notes

Reaction equation

HRID 1428671 reaction equation
[NH2:1][C:2]1[C:3]([C:22]#[C:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[N:4][C:5]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[N:7]=1.CC(C)([O-])C.[K+].O>C(O)(C)(C)C>[C:18]1([CH3:21])[CH:19]=[CH:20][C:15]([C:5]2[N:4]=[C:3]3[CH:22]=[C:23]([CH2:24][CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29])[NH:1][C:2]3=[N:7][C:6]=2[C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 86690320HCID 86690320, compound

Product 1

HCID 86690321HCID 86690321, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

7-(3-Amino-5,6-di-p-tolylpyrazin-2-yl)hept-6-ynoic acid (step 1) (137 mg, 0.343 mmol) in tert-BuOH (3 ml) was treated with potassium tert-butoxide (154 mg, 1.372 mmol) and stirred at reflux for 3 hours. The mixture was added to water (50 ml) and extracted with DCM (×3). The organic solvent was removed under reduced pressure and the crude material was dissolved in EtOH (minimal) and excess of water was added. The resulting suspension was sonicated and filtered, rinsing the filter cake with water (×3). Purification of crude product by chromatograpy on silica eluting with 0-1% MeOH in DCM afforded the titled compound; LC-MS Rt 1.10 mins MS m/z 400.2 [M+H]+; Method 2 minLC_v003

Workup

  1. temperatureat reflux for 3 hours
  2. extractionextracted with DCM (×3)
  3. customThe organic solvent was removed under reduced pressure
  4. dissolutionthe crude material was dissolved in EtOH (minimal) and excess of water
  5. additionwas added
  6. customThe resulting suspension was sonicated
  7. filtrationfiltered
  8. washrinsing the filter cake with water (×3)
  9. customPurification of crude product by chromatograpy on silica eluting with 0-1% MeOH in DCM

Sources & evidence

ORD record
ord-f17182ce5134437eb4ea560ccef60a86
Source dataset
uspto-grants-2015_01
Patent number
US08937069B2

Reaction notes

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