Ethyl orthoformate → HCID 178455732, compound

HRID 81208Notes

Reaction equation

HRID 81208 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][CH:9]([C@H:11]2[CH2:16][CH2:15][C@H:14]([CH3:17])[CH2:13][CH2:12]2)[CH3:10])=[C:6]([NH2:18])[CH:5]=[C:4]([Cl:19])[N:3]=1.[CH2:20](OC(OCC)OCC)C>>[Cl:1][C:2]1[C:7]2[N:8]([CH:9]([C@H:11]3[CH2:16][CH2:15][C@H:14]([CH3:17])[CH2:13][CH2:12]3)[CH3:10])[CH:20]=[N:18][C:6]=2[CH:5]=[C:4]([Cl:19])[N:3]=1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 178463350HCID 178463350, compound

Product 1

HCID 178455732HCID 178455732, compound

Conditions

Temperature
100 °C

Procedure

A suspension of 2,6-dichloro-N3-(1-(trans-4-methylcyclohexyl)ethyl)pyridine-3,4-diamine (35 g, 0.116 mol) in triethylorthoformate (200 mL, 1.16 mol) was stirred at 100° C. for 3 h. TLC (petroleum ether/ethyl acetate=3/1) showed the reaction was complete. The solvent was removed under reduced pressure. The residue was purified by column chromatography (petroleum ether/ethyl acetate=10:1) to give the crude product, which was washed with a mixture of petroleum ether/ethyl acetate=10:1 to afford 4,6-dichloro-3-[1-(trans-4-methylcyclohexyl)ethyl]-3H-imidazo[4,5-c]pyridine. 1H NMR (400 MHz, DMSO-d6) δ: 8.85 (s, 1H), 7.86 (s, 1H), 4.98 (bs, 1H), 1.76-1.67 (m, 3H), 1.58-1.56 (m, 4H), 1.23-1.20 (m, 2H), 1.07-0.99 (m, 2H), 0.84-0.79 (m, 5H). MS ESI calc'd. for C15H19Cl2N3 [M+H]+ 312. found 312.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was purified by column chromatography (petroleum ether/ethyl acetate=10:1)
  3. customto give the crude product, which
  4. washwas washed with a mixture of petroleum ether/ethyl acetate=10:1

Sources & evidence

ORD record
ord-2eb0273d4aa245c0aac85b0eb7f74f5a
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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