Hydrochloric Acid → HCID 90410831, compound

HRID 573996Notes

Reaction equation

HRID 573996 reaction equation
[F:1][C:2]1[C:3]([NH:23][C@@H:24]2[CH2:29][CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25]2)=[N:4][C:5]([NH:14][C:15]2[C:16]([O:21]C)=[N:17][CH:18]=[CH:19][CH:20]=2)=[N:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.Cl>O1CCOCC1>[F:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:6][C:5]([NH:14][C:15]2[C:16](=[O:21])[NH:17][CH:18]=[CH:19][CH:20]=2)=[N:4][C:3]=1[NH:23][C@@H:24]1[CH2:29][CH2:28][CH2:27][NH:26][CH2:25]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90410445HCID 90410445, compound

Product 1

HCID 90410831HCID 90410831, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of (R)-tert-butyl 3-(5-fluoro-2-(2-methoxypyridin-3-ylamino)-6-morpholino pyrimidin-4-ylamino)piperidine-1-carboxylate (Preparation 24b, 0.099 g, 0.30 mmol) and a 4N solution of hydrogen chloride in 1,4-dioxane (70 mL) was stirred at ambient temperature for 3 hours. The solvent was evaporated under reduced pressure and the residue was partitioned between ethyl acetate and a 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 (0.088 g, 93%) as a yellow foam that was used in the next synthetic step without further purification.

Workup

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

Sources & evidence

ORD record
ord-95eb0c3e58174a7ebca628a62077f862
Source dataset
uspto-grants-2015_05
Patent number
US09034311B2

Reaction notes

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