Ethyl orthoformate → HCID 178461251, compound

HRID 81096Notes

Reaction equation

HRID 81096 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][CH2:9][C@H:10]2[CH2:15][CH2:14][C@H:13]([CH3:16])[CH2:12][CH2:11]2)=[C:6]([NH2:17])[CH:5]=[C:4]([Cl:18])[N:3]=1.[CH2:19](OC(OCC)OCC)C>C(OC(=O)C)(=O)C>[Cl:1][C:2]1[C:7]2[N:8]([CH2:9][C@H:10]3[CH2:11][CH2:12][C@H:13]([CH3:16])[CH2:14][CH2:15]3)[CH:19]=[N:17][C:6]=2[CH:5]=[C:4]([Cl:18])[N:3]=1

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 178461256HCID 178461256, compound

Product 1

HCID 178461251HCID 178461251, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 2,6-dichloro-N3-((trans-4-methylcyclohexyl)methyl)pyridine-3,4-diamine (126 g, 0.386 mol) in triethylorthoformate (1.0 L) and acetic anhydride (1.0 L) was stirred at 90° C. for 3 h. The solution was concentrated in vacuo, and the residue was dissolved in DCM/10% NaOH (2.0 L/1.0 L). The organic layer was separated and concentrated. The crude product was purified by a silica gel column, eluting with DCM/petroleum ether (1:1), to give 4,6-dichloro-3-((trans-4-methylcyclohexyl)methyl)-3H-imidazo[4,5-c]pyridine. MS ESI calc'd. for C14H17Cl2N3 [M+H]+ 298. found 298. 1H NMR (400 MHz, CDCl3): 7.96 (s, 1H); 7.66 (m, 1H); 4.28-4.26 (d, 2H); 1.85-1.79 (m, 1H); 1.73-1.71 (d, 2H), 1.70-1.61 (d, 2H), 1.34-1.33 (m, 1H) 1.12-1.02 (m, 2H), 0.94-0.84 (m, 5H).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. dissolutionthe residue was dissolved in DCM/10% NaOH (2.0 L/1.0 L)
  3. customThe organic layer was separated
  4. concentrationconcentrated
  5. customThe crude product was purified by a silica gel column
  6. washeluting with DCM/petroleum ether (1:1)

Sources & evidence

ORD record
ord-ae98ef2f80af48e3bd05a8e39cef6e3f
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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