Cyclohexylamine → HCID 67453476, compound

HRID 2175459Notes

Reaction equation

HRID 2175459 reaction equation
[CH3:1][C:2]1([CH3:14])[O:13][C:6]2=[N:7][CH:8]=[C:9]([CH:11]=O)[CH:10]=[C:5]2[CH:4]=[CH:3]1.[CH:15]1([NH2:21])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.[BH3-]C#N.[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[CH3:1][C:2]1([CH3:14])[O:13][C:6]2=[N:7][CH:8]=[C:9]([CH2:11][NH:21][CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[CH:10]=[C:5]2[CH:4]=[CH:3]1

Participants

6

Reactant 3

HCID 7965CyclohexylamineHCID 5003444Sodium cyanoborohydrideHCID 56925646HCID 56925646, compound

Product 1

HCID 67453476HCID 67453476, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2,2-dimethyl-2H-pyrano[2,3-b]pyridine-6-carbaldehyde 18 (23 mg, 0.121 mmol) in MeOH (1 mL) was added cyclohexylamine (0.014 mL, 0.121 mmol), NaCNBH3 (15 mg, 0.242 mmol) and Zinc chloride (33 mg, 0.242 mmol) and stirred overnight. The solvent was removed by rotary evaporation and the residue dissolved in EtOAc and washed with 1M NaOH, water and brine, dried over MgSO4 and concentrated in vacuo. The product was used in the next step without further purification.

Workup

  1. customThe solvent was removed by rotary evaporation
  2. dissolutionthe residue dissolved in EtOAc
  3. washwashed with 1M NaOH, water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe product was used in the next step without further purification

Sources & evidence

ORD record
ord-5d9b402092044b9fb59953479594c6bb
Source dataset
uspto-grants-2015_06
Patent number
US09062072B2

Reaction notes

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