3-Aminopyridine → HCID 131724640, compound

HRID 2414808Notes

Reaction equation

HRID 2414808 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.[NH2:36][C:37]1[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=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:39]1[CH:40]=[CH:41][CH:42]=[C:37]([NH-:36])[CH:38]=1

Participants

4

Reactant 2

HCID 100093-AminopyridineHCID 6436801Borrelidin2×

Product 1

HCID 131724640HCID 131724640, compound

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

To a mixed anhydride solution prepared from 200 mg (0.41 mmol) of borrelidin according to Example 3 188 mg (2 mmol) of 3-aminopyridin were added. After stirring for 3 hours, the starting borrelidin (Rf=0.43) disappeared and the product (Rf=0.25) 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 100 ml of chloroform, washed with 3×30 ml of water, dried over sodium sulfate and evaporated to dryness. The dry residue was chromatographed on a silica gel column with mixtures of dichloromethane and ethyl acetate of increasing ethyl acetate content. The fractions containing the product eluting with a 1:9 eluting mixture were combined and evaporated to dryness. The structure of the thus-obtained solidifying oily product (144 mg) was confirmed by spectroscopic (PMR, CMR, TS) data.

Workup

  1. additionwere added
  2. customThe reaction mixture was evaporated to dryness
  3. dissolutionThe dry residue was dissolved in 100 ml of chloroform
  4. washwashed with 3×30 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 dichloromethane and ethyl acetate of increasing ethyl acetate content
  8. additionThe fractions containing the product
  9. washeluting with a 1:9 eluting mixture
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-9efb120a78b24870b78e2ddf31a30b82
Source dataset
uspto-grants-2004_11
Patent number
US06815465B1

Reaction notes

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