Ammonium Chloride → HCID 23401036, compound

HRID 750744Notes

Reaction equation

HRID 750744 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:9][C:10]1[C:18]2[C:13](=[N:14][C:15]([CH3:21])=[CH:16][C:17]=2[CH:19]=[O:20])[S:12][C:11]=1[C:22]([NH2:24])=[O:23].[NH4+].[Cl-]>C1COCC1>[NH2:9][C:10]1[C:18]2[C:13](=[N:14][C:15]([CH3:21])=[CH:16][C:17]=2[CH:19]([OH:20])[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[S:12][C:11]=1[C:22]([NH2:24])=[O:23]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 10331631HCID 10331631, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 23401036HCID 23401036, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 314 mg CeCl3 in 3 mL dry THF at −78° C. was added 0.425 mL 3M phenylmagnesium bromide and the reaction was stirred 1.5 h under Ar. Then, 50 mg of 3-amino-4-formyl-6-methyl-thieno[2,3-b]pyridine-2-carboxylic acid amide was added and the reaction was stirred 5 h in the cold and then allowed to warm to room temperature over 0.5 h. Aqueous NH4Cl was added and the reaction was filtered through diatomaceous earth, washing with EtOAc, and the aqueous phase was separated and extracted 3 times with more with EtOAc. The combined organics were dried, and concentrated in vacuo, and the product was purified on a prep plate developed with 5% MeOH—CH2Cl2. Starting material impurity was removed by dissolving the product in EtOAc with a trace MeOH and washing 3 times with aqueous NaHSO3. The organics were dried, concentrated in vacuo, re-dissolved in MeOH—CH2Cl2, filtered, concentrated and dried in vacuo at 60° C. to provide 8.2 mg of the title compound as a yellow solid.

Workup

  1. stirringthe reaction was stirred 5 h in the cold and
  2. filtrationthe reaction was filtered through diatomaceous earth
  3. washwashing with EtOAc
  4. customthe aqueous phase was separated
  5. extractionextracted 3 times with more with EtOAc
  6. customThe combined organics were dried
  7. concentrationconcentrated in vacuo
  8. customthe product was purified on a prep plate
  9. customStarting material impurity was removed
  10. dissolutionby dissolving the product in EtOAc with a trace MeOH
  11. washwashing 3 times with aqueous NaHSO3
  12. customThe organics were dried
  13. concentrationconcentrated in vacuo
  14. dissolutionre-dissolved in MeOH—CH2Cl2
  15. filtrationfiltered
  16. concentrationconcentrated
  17. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-cd4a003d8b584983b66c80c945b75ea3
Source dataset
uspto-grants-2008_07
Patent number
US07405225B2

Reaction notes

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