Hydrochloric Acid → HCID 90410034, compound

HRID 573998Notes

Reaction equation

HRID 573998 reaction equation
C[O:2][C:3]1[C:8]([NH:9][C:10]2[C:15]([CH3:16])=[C:14]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[N:13]=[C:12]([NH:23][C@@H:24]3[CH2:29][CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25]3)[N:11]=2)=[CH:7][CH:6]=[CH:5][N:4]=1.Cl>O1CCOCC1>[CH3:16][C:15]1[C:10]([NH:9][C:8]2[C:3](=[O:2])[NH:4][CH:5]=[CH:6][CH:7]=2)=[N:11][C:12]([NH:23][C@@H:24]2[CH2:29][CH2:28][CH2:27][NH:26][CH2:25]2)=[N:13][C:14]=1[N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90411138HCID 90411138, compound

Product 1

HCID 90410034HCID 90410034, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of (R)-tert-butyl 3-(4-(2-methoxypyridin-3-ylamino)-5-methyl-6-morpholino pyrimidin-2-ylamino)piperidine-1-carboxylate (Preparation 27a, 0.523 g, 1.05 mmol) and a 4N solution of hydrogen chloride in 1,4-dioxane (10 mL) was stirred at ambient temperature for 3 days. The solvent was evaporated and the residue was partitioned between ethyl acetate and water. Solid potassium carbonate was added to the aqueous phase until a basic pH was reached and the aqueous solution was extracted with methylene chloride (×3). The combined organic extracts were dried (Na2SO4) and the solvent was evaporated under reduced pressure to give the title compound (0.110 g, 23%) as a yellow solid that was used in the next synthetic step without further purification.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between ethyl acetate and water
  3. additionSolid potassium carbonate was added to the aqueous phase until a basic pH
  4. extractionthe aqueous solution was extracted with methylene chloride (×3)
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-35706b8160f448128320442d0cb8b9df
Source dataset
uspto-grants-2015_05
Patent number
US09034311B2

Reaction notes

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