Hydrochloric Acid → HCID 59718950, compound

HRID 1852536Notes

Reaction equation

HRID 1852536 reaction equation
[N:1]1([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH:16][CH:17]3[CH2:26][CH2:25][C:20]4(OCC[O:21]4)[CH2:19][CH2:18]3)[N:11]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.Cl.C([O-])(O)=O.[Na+]>C1COCC1>[N:1]1([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH:16][CH:17]3[CH2:18][CH2:19][C:20](=[O:21])[CH2:25][CH2:26]3)[N:11]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 59718957HCID 59718957, compound

Product 1

HCID 59718950HCID 59718950, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of (4-benzotriazol-1-yl-pyrimidin-2-yl)-(1,4-dioxa-spiro[4.5]dec-8-yl)-amine (prepared in a similar manner as described in Example 2) (1.53 g, 4 mmol) in 80 mL of THF was added 25 mL of a 3 M aqueous solution of HCl. The reaction mixture was stirred at RT for 20 minutes. The reaction was heated to reflux for 30 minutes. It was then cooled, and poured onto an aqueous NaHCO3 solution. The resulting mixture was extracted with EtOAc, dried over Na2SO4 and filtered. The solvent was evaporated under reduced pressure until the product began to crystallize out of solution; it was then filtered and dried to give the title product as a white powder (942 mg, 70% yield); mp=204.9-206.5° C.; MS=309 (M+H)+.

Workup

  1. customprepared in a similar manner
  2. temperatureThe reaction was heated
  3. temperatureto reflux for 30 minutes
  4. temperatureIt was then cooled
  5. extractionThe resulting mixture was extracted with EtOAc
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customThe solvent was evaporated under reduced pressure until the product
  9. customto crystallize out of solution
  10. filtrationit was then filtered
  11. customdried

Sources & evidence

ORD record
ord-40985e82c69849ee94381c557d26289d
Source dataset
uspto-grants-2015_02
Patent number
US08962622B2

Reaction notes

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