Hydrochloric Acid → HCID 20477731, compound

HRID 904827Notes

Reaction equation

HRID 904827 reaction equation
C([Li])CCC.C[Si](C([Si](C)(C)C)C(N)=O)(C)C.S1C=CC=CN1N1C2C=C(C(=O)C3C=CC=CC=3)C=CC=2N=C1N.Cl.Cl.[S:44]1[CH:49]=[CH:48][CH:47]=[CH:46][N:45]1[N:50]1[C:54]2[CH:55]=[C:56]([C:59]([OH:70])([CH2:66][C:67]([NH2:69])=[O:68])[C:60]3[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=3)[CH:57]=[CH:58][C:53]=2[N:52]=[C:51]1[NH2:71]>O.O1CCCC1>[S:44]1[CH:49]=[CH:48][CH:47]=[CH:46][N:45]1[N:50]1[C:54]2[CH:55]=[C:56]([C:59]([OH:70])([CH2:66][C:67]([NH2:69])=[O:68])[C:60]3[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=3)[CH:57]=[CH:58][C:53]=2[N:52]=[C:51]1[NH2:71]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 11708267BistrimethylsilylacetamidHCID 20477724HCID 20477724, compoundHCID 20477730HCID 20477730, compoundHCID 178418339Butyllithium

Product 1

HCID 20477731HCID 20477731, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

To a stirred cold (-78° C.) solution of 37.5 ml. of 1.6 molar n-butyl lithium in 50 ml. of tetrahydrofuran was added dropwise over one hour a solution of 50 ml. of tetrahydrofuran containing 14.6 ml. of bistrimethylsilylacetamide. Following the addition, a solution of 4.0 g. of 1-(thiazin-2-yl)-2-amino-6-benzoylbenzimidazole in 300 ml. of tetrahydrofuran was added dropwise over one hour. The reaction mixture was stirred for an additional three hours, and then diluted with 300 ml. of water and allowed to warm to room temperature. The aqueous mixture was acidified with 1 N hydrochloric acid. The organic layer was separated and removed, and the aqueous acid layer was neutralized to pH 7.0 with 1 N sodium hydroxide. The aqueous mixture was extracted two times with ethyl acetate, and the combined extracts were washed with water and with brine, dried, and the solvent was removed by evaporation under reduced pressure to provide an oil. The oil was triturated with diethyl ether and the solid was dissolved in dilute hydrochloric acid. A precipitate formed and was filtered and dried to give 790 mg. of 1-(thiazin-2-yl)-2-amino-6-(α-hydroxy-α-aminocarbonylmethylbenzyl)benzimidazole hydrochloride.

Workup

  1. customTo a stirred cold (-78° C.) solution of 37.5 ml
  2. additionthe addition
  3. additiondiluted with 300 ml
  4. customThe organic layer was separated
  5. customremoved
  6. extractionThe aqueous mixture was extracted two times with ethyl acetate
  7. washthe combined extracts were washed with water and with brine
  8. customdried
  9. customthe solvent was removed by evaporation under reduced pressure
  10. customto provide an oil
  11. customThe oil was triturated with diethyl ether
  12. dissolutionthe solid was dissolved in dilute hydrochloric acid
  13. customA precipitate formed
  14. filtrationwas filtered
  15. customdried
  16. customto give 790 mg

Sources & evidence

ORD record
ord-a3823a0dd9984891bb9583b0fc66c0c6
Source dataset
uspto-grants-1983_12
Patent number
US04420479

Reaction notes

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