Hydrochloric Acid → HCID 58565340, compound

HRID 2175331Notes

Reaction equation

HRID 2175331 reaction equation
Cl.[Cl:2][C:3]1[C:11]2[C:6](=[CH: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.CCOC(C)=O>[Cl:2][C:3]1[C:11]2[C:6](=[CH: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

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58565370HCID 58565370, compound

Product 1

HCID 58565340HCID 58565340, compoundYield 118.6%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent2×

Procedure

Hydrogen chloride (4.0 M) in 1,4-dioxane (0.5 mL, 20 mmol) was added to a solution of tert-butyl {1-[3-chloro-1-(3-fluorophenyl)-1H-indol-2-yl]ethyl}carbamate (36 mg, 0.092 mmol) in 1,4-dioxane (1.0 mL) and the reaction was stirred at room temperature for 1 hour. The mixture was diluted with EtOAc, washed with saturated NaHCO3 solution and water. The combined extracts were dried over MgSO4 and concentrated to give the desired product (31.5 mg). LCMS calculated for C16H12ClFN(M-NH2)+: m/z=272.1. Found: 272.0.

Workup

  1. washwashed with saturated NaHCO3 solution and water
  2. dry with materialThe combined extracts were dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ada3c120e07b4f638e127c833e553417
Source dataset
uspto-grants-2015_06
Patent number
US09062055B2

Reaction notes

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