Hydrochloric Acid → HCID 90409597, compound

HRID 573997Notes

Reaction equation

HRID 573997 reaction equation
CO.C[O:4][C:5]1[C:10]([NH:11][C:12]2[N:17]=[C:16]([NH:18][C@@H:19]3[CH2:24][CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20]3)[C:15]([CH3:32])=[C:14]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)[N:13]=2)=[CH:9][CH:8]=[CH:7][N:6]=1.Cl>O1CCOCC1>[CH3:32][C:15]1[C:14]([N:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)=[N:13][C:12]([NH:11][C:10]2[C:5](=[O:4])[NH:6][CH:7]=[CH:8][CH:9]=2)=[N:17][C:16]=1[NH:18][C@@H:19]1[CH2:24][CH2:23][CH2:22][NH:21][CH2:20]1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 90409974HCID 90409974, compound

Product 1

HCID 90409597HCID 90409597, compoundYield 50.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
40 °C

Procedure

Methanol was added to a stirred mixture of (R)-tert-butyl 3-(2-(2-methoxypyridin-3-ylamino)-5-methyl-6-morpholinopyrimidin-4-ylamino)piperidine-1-carboxylate (Preparation 26a, 0.212 g, 0.42 mmol) and 4N solution of hydrogen chloride in 1,4-dioxane (4 mL) in a sealed tube at ambient temperature until a clear solution was formed. After stirring for an additional 3 hours, further 4N hydrogen chloride solution in 1,4-dioxane (3 mL) was added and the resulting mixture was stirred and heated at 40° C. overnight. The solvents were evaporated under reduced pressure and the residue was partitioned between ethyl acetate and an saturated aqueous solution of sodium hydrogencarbonate. The organic layer was separated and the aqueous phase was washed with ethyl acetate (×2). The combined organic extracts were dried (Na2SO4) and the solvent evaporated under reduced pressure to give the title compound (0.082 g, 37%) as an orange foam that was used in the next synthetic step without further purification.

Workup

  1. customwas formed
  2. stirringthe resulting mixture was stirred
  3. customThe solvents were evaporated under reduced pressure
  4. customthe residue was partitioned between ethyl acetate
  5. customThe organic layer was separated
  6. washthe aqueous phase was washed with ethyl acetate (×2)
  7. dry with materialThe combined organic extracts were dried (Na2SO4)
  8. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-d6b7da6e56384b7d9ae0077f6a87770b
Source dataset
uspto-grants-2015_05
Patent number
US09034311B2

Reaction notes

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