Hydrochloric Acid → HCID 71226770, compound

HRID 2409926Notes

Reaction equation

HRID 2409926 reaction equation
Cl.[F:2][C:3]([F:32])([F:31])[C:4]1[N:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH2:13][C@H:12]([NH:16][C@@H:17]3[CH2:22][CH2:21][CH2:20][CH2:19][C@H:18]3[NH:23]C(=O)OC(C)(C)C)[CH2:11]2)=[CH:6][N:5]=1>O1CCOCC1.CO>[F:32][C:3]([F:2])([F:31])[C:4]1[N:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH2:13][C@H:12]([NH:16][C@@H:17]3[CH2:22][CH2:21][CH2:20][CH2:19][C@H:18]3[NH2:23])[CH2:11]2)=[CH:6][N:5]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86690351HCID 86690351, compound

Product 1

HCID 71226770HCID 71226770, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent2×

Procedure

4 N HCl in dioxane (2.29 mL, 9.15 mmol) was slowly added to a solution of tert-butyl (1R,2R)-2-((S)-1-(2-(trifluoromethyl)pyrimidin-5-yl)piperidin-3-ylamino)cyclohexylcarbamate (0.58 gm, 1.31 mmol) in dioxane (3.52 mL) and MeOH (0.44 mL). After 1 h of stirring the reaction mixture was concentrated and the residue was partitioned between EtOAc and sat. NaHCO3. The aqueous phase was isolated and extracted with EtOAc. All organic phases were combined, washed with saturated aqueous NaCl, dried over MgSO4, filtered and concentrated to give the product (1R,2R)—N1—((S)-1-(2-(trifluoromethyl)pyrimidin-5-yl)piperidin-3-yl)cyclohexane-1,2-diamine (0.44 gm, 1.29 mmol, 99% yield) as a syrup. Anal. Calcd. for C16H24F3N5 m/z 343.2, found: 344.2 (M+H)+.

Workup

  1. concentrationwas concentrated
  2. customthe residue was partitioned between EtOAc and sat. NaHCO3
  3. customThe aqueous phase was isolated
  4. extractionextracted with EtOAc
  5. washwashed with saturated aqueous NaCl
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-da38a7a58fd14e5e979472ae97f9a011
Source dataset
uspto-grants-2014_08
Patent number
US08815909B2

Reaction notes

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