Hydrochloric Acid → HCID 58495545, compound

HRID 1190977Notes

Reaction equation

HRID 1190977 reaction equation
B.CSC.[CH:5]1([O:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]#[N:19])=[N:16][CH:17]=2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.CO.Cl>C1COCC1>[NH2:19][CH2:18][C:15]1[CH:14]=[CH:13][C:12]([O:11][CH:5]2[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]2)=[CH:17][N:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 12423031(Dimethyl sulfide)trihydroboronHCID 58495633HCID 58495633, compound

Product 1

HCID 58495545HCID 58495545, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, add borane-dimethylsulfide complex (20.3 mL, 40.6 mmol, 2M solution in THF) to a solution of 5-cyclohexyloxy-pyridine-2-carbonitrile (0.82 g, 4.06 mmol) in THF (800 mL) at 0° C. Warm the mixture to room temperature and stir overnight. Cool the mixture in an ice-bath, add methanol (15 mL) and concentrated HCl (2 mL). Stir for 2 h, and concentrate in vacuo. Dissolve the residue in saturated aqueous K2CO3. Extract with DCM and wash the organic phase with water and brine. Dry the organic phase over Na2SO4, filter, and concentrate in vacuo to obtain the title compound (0.3 g, 36%). MS (ES+) m/z: 207 (M+H)+.

Workup

  1. temperatureCool the mixture in an ice-bath
  2. stirringStir for 2 h
  3. concentrationconcentrate in vacuo
  4. dissolutionDissolve the residue in saturated aqueous K2CO3
  5. extractionExtract with DCM
  6. washwash the organic phase with water and brine
  7. dry with materialDry the organic phase over Na2SO4
  8. filtrationfilter
  9. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-6bfa34e64c524aaaa7b61a50f8df82a4
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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