Hydrochloric Acid → HCID 178488596, compound

HRID 2174096Notes

Reaction equation

HRID 2174096 reaction equation
[C:1]([C:3]1[CH:50]=[CH:49][C:6]2[N:7](COCC[Si](C)(C)C)[C:8]([C:10]([C:22]3[C:30]([O:31][CH3:32])=[CH:29][C:28]([CH3:33])=[C:27]4[C:23]=3[CH:24]=[CH:25][N:26]4[C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])([NH:15]S(C(C)(C)C)=O)[C:11]([F:14])([F:13])[F:12])=[N:9][C:5]=2[CH:4]=1)#[N:2].C(C1C=CC2N=C(C(C3C(OC)=CC(C)=C4C=3C=CN4C(OC(C)(C)C)=O)(NS(C(C)(C)C)=O)C(F)(F)F)N(COCC[Si](C)(C)C)C=2C=1)#N.Cl.[NH4+].[OH-]>O1CCOCC1.O>[NH2:15][C:10]([C:22]1[C:30]([O:31][CH3:32])=[CH:29][C:28]([CH3:33])=[C:27]2[C:23]=1[CH:24]=[CH:25][N:26]2[C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])([C:8]1[NH:7][C:6]2[CH:49]=[CH:50][C:3]([C:1]#[N:2])=[CH:4][C:5]=2[N:9]=1)[C:11]([F:14])([F:13])[F:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 86701518HCID 86701518, compoundHCID 86701519HCID 86701519, compound

Product 1

HCID 178488596HCID 178488596, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of a mixture of (±)-tert-butyl 4-(1-(5-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)-1-(1,1-dimethylethylsulfinamido)-2,2,2-trifluoroethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate and (±)-tert-butyl 4-(1-(6-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)-1-(1,1-dimethylethylsulfinamido)-2,2,2-trifluoroethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (Example 36-D) (0.37 g, 0.504 mmol) in dioxane (5.04 mL) was added HCl (4.0M in dioxane) (2.52 mL, 10.08 mmol) and this was stirred at room temperature. After 15 minutes this was cooled in an ice bath, neutralized with 30% aq. NH4OH (2.52 mL), diluted with water, extracted twice with EtOAc, dried with MgSO4, filtered and concentrated. The resulting residue was purified by flash chromatography (0-70% EtOAc in heptanes) to provide the title compound. MS (ESI+) m/z 500.2 (M+H).

Workup

  1. temperatureAfter 15 minutes this was cooled in an ice bath
  2. extractionextracted twice with EtOAc
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was purified by flash chromatography (0-70% EtOAc in heptanes)

Sources & evidence

ORD record
ord-30bb8f5f87464d92b4e220c1e9a5228d
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

Loading…