Hydrochloric Acid → HCID 131730801, compound

HRID 1890378Notes

Reaction equation

HRID 1890378 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[N:17]([S:21]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=2)(=[O:23])=[O:22])[CH:16]=[CH:15]3)[CH2:9]1)=O)(C)(C)C.[ClH:34]>C(O)=O.CCOCC>[ClH:34].[NH:8]1[CH2:11][CH:10]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[N:17]([S:21]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:32])([F:33])[F:31])[CH:25]=2)(=[O:22])=[O:23])[CH:16]=[CH:15]3)[CH2:9]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 25069924HCID 25069924, compound2×

Product 1

HCID 131730801HCID 131730801, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 3283Diethyl EtherSolvent2×

Procedure

3-[1-(3-Trifluoromethyl-benzenesulfonyl)-1H-indol-5-yl]-azetidine-1-carboxylic acid tert-butyl ester (compound 13) (400 mg, 0.83 mmol) was dissolved in formic acid (4.7 ml) at 0° C. and stirred for 2 hours. The reaction mixture was evaporated to dryness at 30° C. The residue was dissolved in ethyl acetate (50 ml), and washed with a 1 molar aqueous solution of NaOH (10 ml). The organic layer was dried over magnesium sulphate, filtered, and evaporated to dryness to yield the crude product (231 mg, 82%). The crude product was dissolved in ether (50 ml), treated with a solution of hydrochloric acid in ether, and the precipitate was collected to give the product (151 mg, 44%).

Workup

  1. customThe reaction mixture was evaporated to dryness at 30° C
  2. dissolutionThe residue was dissolved in ethyl acetate (50 ml)
  3. washwashed with a 1 molar aqueous solution of NaOH (10 ml)
  4. dry with materialThe organic layer was dried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customto yield the crude product (231 mg, 82%)
  8. customthe precipitate was collected

Sources & evidence

ORD record
ord-ae1f84dcc592425e9c4afa53b810b5a4
Source dataset
uspto-grants-2013_08
Patent number
US08507469B2

Reaction notes

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