Hydrochloric Acid → HCID 67000197, compound

HRID 558163Notes

Reaction equation

HRID 558163 reaction equation
[N:1]1([CH2:6][CH2:7][NH:8][C:9]2[N:14]=[C:13]([C:15]3[S:19][C:18]4[C:20]([CH2:24][C:25]5[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=5[C@@H:32]([NH:37][S@](C(C)(C)C)=O)[C:33]([F:36])([F:35])[F:34])=[CH:21][CH:22]=[CH:23][C:17]=4[CH:16]=3)[C:12]([F:44])=[CH:11][N:10]=2)[CH:5]=[CH:4][N:3]=[N:2]1.Cl>CO>[N:1]1([CH2:6][CH2:7][NH:8][C:9]2[N:14]=[C:13]([C:15]3[S:19][C:18]4[C:20]([CH2:24][C:25]5[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=5[C@@H:32]([NH2:37])[C:33]([F:34])([F:35])[F:36])=[CH:21][CH:22]=[CH:23][C:17]=4[CH:16]=3)[C:12]([F:44])=[CH:11][N:10]=2)[CH:5]=[CH:4][N:3]=[N:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67000042HCID 67000042, compound

Product 1

HCID 67000197HCID 67000197, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Stir a mixture of (S)—N—((R)-1-(2-((2-(2-(2-(1H-1,2,3-Triazol-1-yl)ethylamino)-5-fluoropyrimidin-4-yl)benzo[b]thiophen-7-yl)methyl)-4-fluorophenyl)-2,2,2-trifluoroethyl)-2-methylpropane-2-sulfinamide (10.5 g, 16.52 mmol) and HCl (16.52 mL, 66.07 mmol, in dioxane) in methanol (100 mL) for 2 h. Concentrate the mixture and dilute with NaOH (1 N). Extract the product with ethyl acetate (150 mL×3). Wash the organic layer with 1:1 water/aqueous saturated sodium chloride and aqueous saturated sodium chloride. Dry over Na2SO4, filter, and concentrate. Dissolve the material with heat in DCM/hexanes and solidify the material in 3 h upon cooling. Filter the solid to give the title compound (8.1 g tan solid, 92%). MS (ES) m/z 546 [M+1]+.

Workup

  1. concentrationConcentrate the mixture
  2. additiondilute with NaOH (1 N)
  3. extractionExtract the product with ethyl acetate (150 mL×3)
  4. washWash the organic layer with 1:1 water/aqueous saturated sodium chloride and aqueous saturated sodium chloride
  5. dry with materialDry over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate
  8. dissolutionDissolve the material
  9. temperaturewith heat in DCM/hexanes
  10. customin 3 h
  11. temperatureupon cooling
  12. filtrationFilter the solid

Sources & evidence

ORD record
ord-0268ad85b3864f748c9863fcd6e5dfd7
Source dataset
uspto-grants-2011_11
Patent number
US08063035B2

Reaction notes

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