2-Pyridinemethanamine → HCID 131724639, compound

HRID 2414807Notes

Reaction equation

HRID 2414807 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]=[CH:38][C:37]=1[CH2:42][NH2:43]>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]=[CH:38][C:37]=1[CH2:42][NH-:43]

Participants

4

Reactant 2

HCID 195092-PyridinemethanamineHCID 6436801Borrelidin2×

Product 1

HCID 131724639HCID 131724639, 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 3 206 μl (2 mmol, 216 mg) of 2-picolylamine were added. After stirring for 3 hours, the starting borrelidin (Rf=0.52) disappeared and the product (Rf=0.29) appeared, which was proved by thin-layer chromatography (silica gel plate, eluent system: chloroform/methanol 3:7). 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 chloroform and ethyl acetate of increasing ethyl acetate content. The fractions containing the product eluting with a 1:1 eluting mixture were combined and evaporated to dryness. The structure of the thus-obtained solidifying oily product (188 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 chloroform and ethyl acetate of increasing ethyl acetate content
  8. additionThe fractions containing the product
  9. washeluting with a 1:1 eluting mixture
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-bd4ddd922204476c9697415e257002d4
Source dataset
uspto-grants-2004_11
Patent number
US06815465B1

Reaction notes

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