Hydrochloric Acid → HCID 58565347, compound

HRID 2175342Notes

Reaction equation

HRID 2175342 reaction equation
Cl.[Cl:2][C:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[C:4]=1[CH:19]([NH:21]C(=O)OC(C)(C)C)[CH3:20]>O1CCOCC1>[Cl:2][C:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[C:4]=1[CH:19]([NH2:21])[CH3:20]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58565361HCID 58565361, compound

Product 1

HCID 58565347HCID 58565347, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

4.0 M Hydrogen chloride in 1,4-dioxane (1.0 mL, 4.0 mmol) was added to a solution of tert-butyl {1-[3-chloro-1-(3-fluorophenyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]ethyl}carbamate (26 mg, 0.067 mmol) in 1,4-dioxane (1.0 mL). The reaction was stirred at room temperature overnight. The mixture was then partitioned between EtOAc and water. The aqueous layer was adjusted to pH 9 with saturated NaHCO3 solution and then extracted with EtOAc. The combined organic layers were dried over MgSO4 and concentrated to give the desired amine (7 mg, 40%). LCMS calculated for C15H14ClFN3(M+H)+: m/z=290.1. Found: 290.0.

Workup

  1. customThe mixture was then partitioned between EtOAc and water
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-278cffa1c1564a459bdd3d13b74b9a19
Source dataset
uspto-grants-2015_06
Patent number
US09062055B2

Reaction notes

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