3-Pyridinemethanamine → HCID 131724642, compound

HRID 2414810Notes

Reaction equation

HRID 2414810 reaction equation
[CH3:1][C@@H:2]1[CH2:20][C@H:19]([CH3:21])[C@@H:18]([OH:22])[CH2:17][C:15](=[O:16])[O:14][C@H:13]([C@H:23]2[C@H:27]([C:28]([OH:30])=[O:29])[CH2:26][CH2:25][CH2:24]2)[CH2:12][CH:11]=[CH:10][CH:9]=[C:8]([C:31]#[N:32])[C@H:7]([OH:33])[C@@H:6]([CH3:34])[CH2:5][C@H:4]([CH3:35])[CH2:3]1.[N:36]1[CH:41]=[CH:40][CH:39]=[C:38]([CH2:42][NH2:43])[CH:37]=1>C(Cl)(Cl)Cl.CO>[CH3:1][C@@H:2]1[CH2:20][C@H:19]([CH3:21])[C@@H:18]([OH:22])[CH2:17][C:15](=[O:16])[O:14][C@H:13]([C@H:23]2[C@H:27]([C:28]([OH:30])=[O:29])[CH2:26][CH2:25][CH2:24]2)[CH2:12][CH:11]=[CH:10][CH:9]=[C:8]([C:31]#[N:32])[C@H:7]([OH:33])[C@@H:6]([CH3:34])[CH2:5][C@H:4]([CH3:35])[CH2:3]1.[N:36]1[CH:41]=[CH:40][CH:39]=[C:38]([CH2:42][NH-:43])[CH:37]=1

Participants

4

Reactant 2

HCID 310183-PyridinemethanamineHCID 6436801Borrelidin2×

Product 1

HCID 131724642HCID 131724642, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

To a mixed anhydride solution prepared from 4.0 g (8.2 mmol) of borrelidin according to Example 34.2 ml (41.2 mmol, 4.46 g) of 3-picolylamine were added. After stirring for 3 hours, the starting borrelidin (Rf=0.43) disappeared and the product (Rf=0.24) appeared, which was proved by thin-layer chromatography (silica gel plate, eluent system: chloroform/methanol 95:5). The reaction mixture was evaporated to dryness. The dry residue was dissolved in 500 ml of chloroform, washed with 3×1500 ml of water, dried over sodium sulfate and evaporated to dryness. The dry residue was chromatographed on a silica gel column with mixtures of chloroform and ethyl acetate of increasing ethyl acetate content. The fractions containing the product eluting with a 2:8 eluting mixture were combined and evaporated to dryness. To the thus-obtained solidifying oily substance (3.62 g) 4 ml of ethyl acetate and 20 ml of n-hexane were added, the solid material was triturated and then filtered. In this way 3.04 g product were obtained. Mp.: 99-105° C.

Workup

  1. additionwere added
  2. customThe reaction mixture was evaporated to dryness
  3. dissolutionThe dry residue was dissolved in 500 ml of chloroform
  4. washwashed with 3×1500 ml of water
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness
  7. customThe dry residue was chromatographed on a silica gel column with mixtures of chloroform and ethyl acetate of increasing ethyl acetate content
  8. additionThe fractions containing the product
  9. washeluting with a 2:8 eluting mixture
  10. customevaporated to dryness
  11. additionTo the thus-obtained solidifying oily substance (3.62 g) 4 ml of ethyl acetate and 20 ml of n-hexane were added
  12. customthe solid material was triturated
  13. filtrationfiltered

Sources & evidence

ORD record
ord-f223aeafd59145a582aac487db77ac38
Source dataset
uspto-grants-2004_11
Patent number
US06815465B1

Reaction notes

Loading…