Hydrochloric Acid → HCID 11983233, compound

HRID 1866797Notes

Reaction equation

HRID 1866797 reaction equation
C(O[C:6](=O)[N:7]([CH2:9][CH2:10][C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=1[S:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1)C)(C)(C)C.C(OCC)C.Cl>CO>[F:17][C:15]1[CH:14]=[CH:13][C:12]([S:18][C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[NH:21][CH:20]=2)=[C:11]([CH2:10][CH2:9][NH:7][CH3:6])[CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 69026414HCID 69026414, compound

Product 1

HCID 11983233HCID 11983233, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

{2-[5-Fluoro-2-(1H-indol-3-ylsulfanyl)-phenyl]-ethyl}-methyl-carbamic acid tert-butyl ester (99 mg, 0.24 mmol) is dissolved in methanol (1.5 mL) and diethyl ether saturated with hydrochloric acid (0.5 mL) is added. The mixture is stirred at ambient temperature for 2 hours and concentrated in vacuo. Water (5 mL) is added to the remanence and the mixture is basified by addition of aqueous ammonia (25%). The aqueous fraction is extracted with ethyl acetate (3×10 mL). The combined organic fractions are dried (MgSO4) and concentrated in vacuo. The product is purified by preparative HPLC or silica gel chromatography eluting with ethyl acetate-ethanol-triethyl amine (100:5:5) to give 62 mg (83%) of the title compound.

Workup

  1. concentrationconcentrated in vacuo
  2. additionWater (5 mL) is added to the remanence
  3. additionthe mixture is basified by addition of aqueous ammonia (25%)
  4. extractionThe aqueous fraction is extracted with ethyl acetate (3×10 mL)
  5. dry with materialThe combined organic fractions are dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe product is purified by preparative HPLC or silica gel chromatography
  8. washeluting with ethyl acetate-ethanol-triethyl amine (100:5:5)

Sources & evidence

ORD record
ord-dcb312e03964499cb26d0ebe1e955d00
Source dataset
uspto-grants-2009_12
Patent number
US07629473B2

Reaction notes

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