Cyanogen Bromide → N7-(1-Ethyl-propyl)-5-methyl-3-(2,4,6-trimethyl-phenyl)-3H-imidazo[4,5-b]pyridine-2,7-diamine

HRID 2307998Notes

Reaction equation

HRID 2307998 reaction equation
[CH2:1]([CH:3]([NH:6][C:7]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]([NH:14][C:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=2[CH3:23])[C:8]=1[NH2:24])[CH2:4][CH3:5])[CH3:2].Br[C:26]#[N:27]>C(#N)C>[CH2:1]([CH:3]([NH:6][C:7]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]2[N:14]([C:15]3[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=3[CH3:23])[C:26]([NH2:27])=[N:24][C:8]=12)[CH2:4][CH3:5])[CH3:2]

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 21912187N4-(1-ethyl-propyl)-6-methyl-N2-(2,4,6-trimethyl-phenyl)-pyridine-2,3,4-triamine

Product 1

HCID 21912344N7-(1-Ethyl-propyl)-5-methyl-3-(2,4,6-trimethyl-phenyl)-3H-imidazo[4,5-b]pyridine-2,7-diamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared by reacting N4-(1-ethyl-propyl)-6-methyl-N2-(2,4,6-trimethyl-phenyl)-pyridine-2,3,4-triamine with BrCN in acetonitrile at room temperature overnight. The mixture was quenched with water and adjusted to pH 8.0 with saturated sodium bicarbonate and extracted with ethyl acetate. The organic layer was separated, dried and concentrated to give crude material. The material was purified through silica gel column chromatography to give the title compound as a brown solid, mp. 158-160° C.; Anal. For C21H29N5 ¼H2O calc. C, 70.85; H, 8.35; N, 19.67; found: C, 71.07; H, 8.30; N, 19.63.

Workup

  1. customThe title compound was prepared
  2. customat room temperature
  3. customovernight
  4. customThe mixture was quenched with water
  5. extractionextracted with ethyl acetate
  6. customThe organic layer was separated
  7. customdried
  8. concentrationconcentrated
  9. customto give crude material
  10. customThe material was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-1aca15a54bed47e9b871fff5c81e43ed
Source dataset
uspto-grants-2004_12
Patent number
US06833378B2

Reaction notes

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