2,3-Diaminopyridine → HCID 24960136, compound

HRID 1430628Notes

Reaction equation

HRID 1430628 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([O:8][C:9]([CH3:14])([CH3:13])[C:10]([OH:12])=O)[CH:5]=[CH:4][CH:3]=1.[NH2:15][C:16]1[C:21]([NH2:22])=[CH:20][CH:19]=[CH:18][N:17]=1.CCN=C=NCCCN(C)C>CN(C=O)C>[NH2:22][C:21]1[C:16]([NH:15][C:10](=[O:12])[C:9]([O:8][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([Cl:1])[N:7]=2)([CH3:14])[CH3:13])=[N:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 99562,3-DiaminopyridineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 23404740HCID 23404740, compound

Product 1

HCID 24960136HCID 24960136, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

2-(6-Chloro-pyridin-2-yloxy)-2-methyl-propionic acid (0.53 g, 2.4 mmol) and 2,3-diaminopyridine (0.268 g, 2.4 mmol) were dissolved in DMF (5 ml) cooled to 0° C. and added EDCI (0.62 g, 3.2 mmol) and stirred for 4 h. The reaction mixture was extracted in EtOAc (30 ml) and washed with brine (2×10 ml) dried over Na2SO4 and concentrated under reduced pressure to obtain crude product. The product was purified on silica gel to yield N-(3-Amino-pyridin-2-yl)-2-(6-chloro-pyridin-2-yloxy)-2-methyl-propionamide (0.54 g, 72%). 1H NMR (400 MHz, CDCl3): 4.84 (brs, 2H), 6.67 (dd, J=4.8 and 7.6 Hz, 1H), 6.78 (d, J=8.4 Hz, 1H), 7.02 (d, J=8. Hz, 1H), 7.40 (d, J=8. Hz, 1H), 7.61 (d, J=8 Hz, 1H), 7.996 (dd, J=4.8 Hz and 7.6 Hz, 1H). MS (EI) m/z: 307 (M+1).

Workup

  1. extractionThe reaction mixture was extracted in EtOAc (30 ml)
  2. washwashed with brine (2×10 ml)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto obtain crude product
  6. customThe product was purified on silica gel

Sources & evidence

ORD record
ord-3924aa1135b14ebfb2be179fc06c264f
Source dataset
uspto-grants-2015_01
Patent number
US08940900B2

Reaction notes

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