Hydrochloric Acid → HCID 86639830, compound

HRID 424655Notes

Reaction equation

HRID 424655 reaction equation
[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8](S(Cl)(=O)=O)[N:9]=1)(=[O:3])[CH3:2].[CH2:14]([S:21][C:22]1[N:27]=[C:26]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])[CH:25]=[C:24]([NH:33][C@H:34]([CH3:37])[CH2:35]O)[N:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.S(Cl)(Cl)(=O)=O.Cl.N1C=CC=C[CH:45]=1>C1COCC1>[CH2:14]([S:21][C:22]1[N:27]=[C:26]([NH:28][S:29]([C:32]2[S:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[N:9][C:8]=2[CH3:7])(=[O:31])=[O:30])[CH:25]=[C:24]([NH:33][C@H:34]([CH3:37])[CH2:35][CH3:45])[N:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 24648Sulfuryl chlorideHCID 57833159HCID 57833159, compoundHCID 84728117HCID 84728117, compound

Product 1

HCID 86639830HCID 86639830, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(Acetylamino)-1,3-thiazole-4-sulfonyl chloride (0.19 g) was added to a solution of the subtitle product of Example 3 step (0.2 g) in pyridine (4 ml) and N,N-dimethylaminopyridine (60 mg). The reaction mixture was stirred for 4 days. To this reaction more sulfonyl chloride (0.75 g) was added and stirred for 2 days. To this reaction was added aqueous hydrochloric acid (1M, 20 ml) and THF (20 ml). This was stirred for 18 h before the solvent was evaporated and the residue diluted in EtOAc (100 ml). This was washed with H2O (3×20 ml) and brine (10 ml). The organic layer was dried (MgSO4) and concentrated to yield a solid. This material was purified by reverse phase HPLC (90% to 5% 0.02M ammonium hydroxide/acetonitrile) to yield the title compound as a solid. Yield: 20 mg.

Workup

  1. additionwas added
  2. stirringstirred for 2 days
  3. stirringThis was stirred for 18 h before the solvent
  4. customwas evaporated
  5. additionthe residue diluted in EtOAc (100 ml)
  6. washThis was washed with H2O (3×20 ml) and brine (10 ml)
  7. dry with materialThe organic layer was dried (MgSO4)
  8. concentrationconcentrated
  9. customto yield a solid
  10. customThis material was purified by reverse phase HPLC (90% to 5% 0.02M ammonium hydroxide/acetonitrile)

Sources & evidence

ORD record
ord-0098535def184d3a9f4bc835c334bd38
Source dataset
uspto-grants-2012_01
Patent number
US08106063B2

Reaction notes

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