Hydrochloric Acid → 1-[5-(1,1-Difluoro-6-aza-spiro[2.5]oct-6-yl)-pyridin-2-yl]-1,2,3,4-tetrahydroquinoxaline

HRID 40548Notes

Reaction equation

HRID 40548 reaction equation
[F:1][C:2]1([F:29])[C:4]2([CH2:9][CH2:8][N:7]([C:10]3[CH:11]=[CH:12][C:13]([N:16]4[C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19](C(O)=O)[CH2:18][CH2:17]4)=[N:14][CH:15]=3)[CH2:6][CH2:5]2)[CH2:3]1.Cl>ClCCl.O1CCOCC1>[F:29][C:2]1([F:1])[C:4]2([CH2:9][CH2:8][N:7]([C:10]3[CH:11]=[CH:12][C:13]([N:16]4[C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[NH:19][CH2:18][CH2:17]4)=[N:14][CH:15]=3)[CH2:6][CH2:5]2)[CH2:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 676057664-[5-(1,1-difluoro-6-aza-spiro[2.5]oct-6-yl)-pyridin-2-yl]-3,4-dihydro-2H-quinoxaline-1-carboxylic acid

Product 1

HCID 676059371-[5-(1,1-Difluoro-6-aza-spiro[2.5]oct-6-yl)-pyridin-2-yl]-1,2,3,4-tetrahydroquinoxaline

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

1.48 g of tert-butyl ester of 4-[5-(1,1-difluoro-6-aza-spiro[2.5]oct-6-yl)-pyridin-2-yl]-3,4-dihydro-2H-quinoxaline-1-carboxylic acid is put in 16 mL of dichloromethane. 24 mL of 4M hydrochloric acid in dioxane is added at +4° C. The solution is stirred at room temperature for 4 h and evaporated to dryness. The residue is taken up in a saturated solution of sodium hydrogen carbonate to basic pH. The solution is extracted twice with dichloromethane, washed with water, dried over magnesium sulfate, filtered and evaporated to dryness. 1.4 g of 1-[5-(1,1-difluoro-6-aza-spiro[2.5]oct-6-yl)-pyridin-2-yl]-1,2,3,4-tetrahydroquinoxaline is obtained.

Workup

  1. customevaporated to dryness
  2. extractionThe solution is extracted twice with dichloromethane
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-5d483bc060bf428eac65f282ef3ffcdf
Source dataset
uspto-grants-2013_09
Patent number
US08530473B2

Reaction notes

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