Ethylenediamine → HCID 58495532, compound

HRID 1190956Notes

Reaction equation

HRID 1190956 reaction equation
B.CSC.[CH:5]1([S:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]#[N:19])=[N:16][CH:17]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1.C(N)CN>C1COCC1>[NH2:19][CH2:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][S:10][CH:5]2[CH2:9][CH2:8][CH2:7][CH2:6]2)=[CH:17][N:16]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 12423031(Dimethyl sulfide)trihydroboronHCID 58495624HCID 58495624, compound

Product 1

HCID 58495532HCID 58495532, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add borane-dimethylsulfide complex (6.9 mL, 13.7 mmol, 2M solution in THF) to a solution of 5-cyclopentylthiomethyl-pyridine-2-carbonitrile (1 g, 4 mmol) in THF (12 mL) at room temperature under a nitrogen atmosphere. Stir the solution at room temperature for 16 h. Concentrate the solution in vacuo, dissolve the residue in chloroform (50 mL), add ethylenediamine (0.72 g, 12 mmol) and stir at 50° C. for 1 h. Wash the mixture with water (10 mL), dry the organic phase over Na2SO4 and concentrate in vacuo. Purify the residue by SCX chromatography followed by chromatography on silica gel (10 g) eluting with DCM/2M ammonia in methanol (1:0 to 9:1 gradient) to obtain the title compound (0.24 g, 27%). MS (ES+) m/z: 223.1 (M+H)+.

Workup

  1. concentrationConcentrate the solution in vacuo
  2. dissolutiondissolve the residue in chloroform (50 mL)
  3. stirringstir at 50° C. for 1 h
  4. washWash the mixture with water (10 mL)
  5. dry with materialdry the organic phase over Na2SO4
  6. concentrationconcentrate in vacuo
  7. customPurify the residue by SCX chromatography
  8. washeluting with DCM/2M ammonia in methanol (1:0 to 9:1 gradient)

Sources & evidence

ORD record
ord-d3d2f4cffe2e41b2896d32f7001beb4a
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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