Acetic Acid → HCID 178463362, compound

HRID 1852813Notes

Reaction equation

HRID 1852813 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-60e2d5e4f0154b0a9e530aac2b1807f9
Source dataset
uspto-grants-2015_02
Patent number
US08962611B2

Reaction notes

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