Pyridine → HCID 22380119, compound

HRID 1988759Notes

Reaction equation

HRID 1988759 reaction equation
[NH2:1][C:2]1[C:7]([NH:8][CH2:9][CH3:10])=[CH:6][N:5]=[C:4]([C:11](=[O:13])[CH3:12])[CH:3]=1.[S:14]1[CH:18]=[CH:17][N:16]=[C:15]1[C:19]1[N:20]([CH2:24][C:25](O)=O)[CH:21]=[CH:22][N:23]=1.CCN=C=NCCCN(C)C.N1C=CC=CC=1>O>[CH2:9]([N:8]1[C:7]2[CH:6]=[N:5][C:4]([C:11](=[O:13])[CH3:12])=[CH:3][C:2]=2[N:1]=[C:25]1[CH2:24][N:20]1[CH:21]=[CH:22][N:23]=[C:19]1[C:15]1[S:14][CH:18]=[CH:17][N:16]=1)[CH3:10]

Participants

6

Reactant 4

HCID 1049PyridineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 22379906HCID 22379906, compoundHCID 22380078HCID 22380078, compound

Product 1

HCID 22380119HCID 22380119, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-(4-amino-5-ethylamino-pyridin-2-yl)-ethanone (54 mg, 0.3 mmol), (2-thiazol-2-yl-imidazol-1-yl)-acetic acid (61 mg, 0.3 mmol), EDCI (60 mg, 0.3 mmol) and pyridine (2 mL) is stirred at room temperature for 72 hr and then poured into water. The aqueous layer is extracted with ethyl acetate and the combined organic layers are dried over Na2SO4. Solvent is evaporated in vacuo and the residue is taken up in acetic acid (5 mL). The mixture is heated to reflux for 16 hr and saturated NaHCO3 solution is added to neutralize the reaction. The aqueous solution is extracted with ethyl acetate and the combined organic layers are dried over Na2SO4. Solvent is removed in vacuo and purification by preparative TLC provides the product as white solid. 1H NMR (CDCl3) δ 8.79 (d, 2H), 8.47 (d, 1H), 7.83 (d, 1H), 7.40 (d, 1H), 7.19 (d, 1H), 7.15 (d, 1H), 6.39 (s, 2H), 4.02 (q, 2H), 2.77 (s, 3H), 1.86 (t, 3H). LRMS 353.2 (MH+).

Workup

  1. extractionThe aqueous layer is extracted with ethyl acetate
  2. dry with materialthe combined organic layers are dried over Na2SO4
  3. customSolvent is evaporated in vacuo
  4. temperatureThe mixture is heated
  5. temperatureto reflux for 16 hr
  6. additionsaturated NaHCO3 solution is added
  7. customthe reaction
  8. extractionThe aqueous solution is extracted with ethyl acetate
  9. dry with materialthe combined organic layers are dried over Na2SO4
  10. customSolvent is removed in vacuo and purification by preparative TLC

Sources & evidence

ORD record
ord-bbb2b1b8bea344f0aecaa55f6e7874ed
Source dataset
uspto-grants-2010_01
Patent number
US07642267B2

Reaction notes

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