Ammonium Chloride → HCID 10087836, compound

HRID 750745Notes

Reaction equation

HRID 750745 reaction equation
[CH2:1]([Mg]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][C:11]1[C:19]2[C:14](=[N:15][C:16]([CH3:22])=[CH:17][C:18]=2[CH:20]=[O:21])[S:13][C:12]=1[C:23]([NH2:25])=[O:24].[NH4+].[Cl-]>C1COCC1>[NH2:10][C:11]1[C:19]2[C:14](=[N:15][C:16]([CH3:22])=[CH:17][C:18]=2[CH:20]([OH:21])[CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[S:13][C:12]=1[C:23]([NH2:25])=[O:24]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 10331631HCID 10331631, compoundHCID 178418336HCID 178418336, compound

Product 1

HCID 10087836HCID 10087836, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 344 mg CeCl3 in 3 mL dry THF at −78° was added 0.70 mL 2 M benzylmagnesium chloride and the reaction was stirred 1.5 h under Ar. Then, 41 mg of 3-amino-4-formyl-6-methyl-thieno[2,3-b]pyridine-2-carboxylic acid amide (see Example 16) was added and the reaction was stirred 3.5 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 more with EtOAc. The combined organics were dried, concentrated in vacuo, and re-dissolved in EtOAc with a trace MeOH and washed 3 times with aqueous NaHSO3. This was dried, concentrated in vacuo, and the product was purified on a prep plate developed with 5% MeOH—CH2Cl2. The product was re-dissolved in MeOH—CH2Cl2, filtered, concentrated and dried in vacuo at 60° C. providing 16.3 mg of the title compound as an orange solid.

Workup

  1. stirringthe reaction was stirred 3.5 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 more with EtOAc
  6. customThe combined organics were dried
  7. concentrationconcentrated in vacuo
  8. dissolutionre-dissolved in EtOAc with a trace MeOH
  9. washwashed 3 times with aqueous NaHSO3
  10. customThis was dried
  11. concentrationconcentrated in vacuo
  12. customthe product was purified on a prep plate
  13. dissolutionThe product was re-dissolved in MeOH—CH2Cl2
  14. filtrationfiltered
  15. concentrationconcentrated
  16. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-8e107cadf78644ed9b31be8eee8d63cd
Source dataset
uspto-grants-2008_07
Patent number
US07405225B2

Reaction notes

Loading…