Hydrochloric Acid → HCID 24960268, compound

HRID 1947001Notes

Reaction equation

HRID 1947001 reaction equation
Cl.O1[C:6]2([CH2:11][CH2:10][CH:9]([NH:12][C:13]3[N:18]=[C:17]([N:19]4[C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[CH:21]=[N:20]4)[CH:16]=[CH:15][N:14]=3)[CH2:8][CH2:7]2)[O:5]CC1.[OH-].[Na+]>C1COCC1>[N:19]1([C:17]2[CH:16]=[CH:15][N:14]=[C:13]([NH:12][CH:9]3[CH2:8][CH2:7][C:6](=[O:5])[CH2:11][CH2:10]3)[N:18]=2)[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[N:20]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24960269HCID 24960269, compound

Product 1

HCID 24960268HCID 24960268, compoundYield 102.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

Aqueous HCl (3 M, 40 mL) was added to (1,4-dioxaspiro[4.5]dec-8-yl)-(4-indazol-1-yl-pyrimidin-2-yl)-amine (1.89 g, 5 mmol) in THF (40 mL), and the resulting mixture heated to 80° C. for 1 h. The reaction mixture was cooled and poured onto a mixture of ice and aqueous NaOH (1 M, 120 mL), and the resulting suspension filtered. The collected solids were washed with water, taken up in DCM/MeOH, and a portion of the solvent evaporated under reduced pressure. The resulting suspension was filtered, the collected solids washed with hexanes, and dried under reduced pressure to give 4-(4-indazol-1-ylpyrimidin-2-ylamino)-cyclohexanone (1.57 g, 95% yield) as a white powder. MS=308 [M+H]+; MP=211.8-213.2° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationthe resulting suspension filtered
  3. washThe collected solids were washed with water
  4. customa portion of the solvent evaporated under reduced pressure
  5. filtrationThe resulting suspension was filtered
  6. washthe collected solids washed with hexanes
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-c920e918d86e4778bdf268c0f0c25940
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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