Acetic Acid → HCID 178463362, compound

HRID 81206Notes

Reaction equation

HRID 81206 reaction equation
[BH3-]C#N.[Na+].[Cl:5][C:6]1[C:11]([N:12]=[C:13]([C@H:15]2[CH2:20][CH2:19][C@H:18]([CH3:21])[CH2:17][CH2:16]2)[CH3:14])=[C:10]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:9]=[C:8]([Cl:30])[N:7]=1.C(O)(=O)C>C(O)C>[Cl:5][C:6]1[C:11]([NH:12][CH:13]([C@H:15]2[CH2:16][CH2:17][C@H:18]([CH3:21])[CH2:19][CH2:20]2)[CH3:14])=[C:10]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:9]=[C:8]([Cl:30])[N:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 178463361HCID 178463361, compound

Product 1

HCID 178463362HCID 178463362, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

NaCNBH3 (100 g, 1.59 mol) was added to a mixture of tert-butyl (2,6-dichloro-3-((1-(trans-4-methylcyclohexyl)ethylidene)amino)pyridin-4-yl)carbamate (80 g, 0.2 mol) and acetic acid (60 mL) in ethanol (1.2 L). The mixture was heated to 50° C. for 4 h. TLC (petroleum ether/ethyl acetate=8:1) showed the reaction was complete. The reaction mixture was cooled down, poured into ice water, and then extracted with ethyl acetate. The combined organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to give crude tert-butyl (2,6-dichloro-3-((1-(trans-4-methylcyclohexyl)ethyl)amino)pyridin-4-yl)carbamate, which was used for the next step without further purification.

Workup

  1. temperatureThe reaction mixture was cooled down
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b9cc0b26c1ff428790bf6bd6fc925fe1
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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