2,3-Diaminopyridine → HCID 178458530, compound

HRID 1644590Notes

Reaction equation

HRID 1644590 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[C:2]=1[NH2:8].[CH2:9]([O:16][C:17]1[CH:18]=[CH:19][C:20]([O:26][CH:27]([CH3:29])[CH3:28])=[C:21]([CH:25]=1)[C:22](O)=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.O.C(O)C.C(O)(=O)C>[CH2:9]([O:16][C:17]1[CH:18]=[CH:19][C:20]([O:26][CH:27]([CH3:29])[CH3:28])=[C:21]([C:22]2[NH:8][C:2]3=[N:1][CH:6]=[CH:5][CH:4]=[C:3]3[N:7]=2)[CH:25]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

9

Reactant 4

HCID 99562,3-DiaminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 59243115HCID 59243115, compound

Product 1

HCID 178458530HCID 178458530, compoundYield 32.2%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution (20 ml) of pyridine-2,3-diamine (0.6 g), 5-(benzyloxy)-2-isopropoxybenzoic acid (1.31 g), 1-hydroxybenztriazole hydrate (0.93 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.32 g) in N,N-dimethylformamide was stirred at room temperature for 18 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and concentrated to give as pale-brown crystals. The obtained crystals were added to acetic acid (2.5 ml)-ethanol (2.5 ml), and the mixture was subjected to microwave irradiation in a sealed reaction container at 180° C. for 40 min. The reaction mixture was concentrated, and the precipitated crystals were collected by filtration and washed with ethanol to give the title compound (0.53 g, yield 32%) as colorless crystals. melting point 160-162° C. purity 95%. M+H: 360. 1H NMR (CDCl3) δ: 1.50 (6H, d, J=6.2 Hz), 4.64-4.85 (1H, m), 5.16 (2H, s), 6.95-7.56 (8H, m), 8.08 (1H, d, J=7.9 Hz), 8.21 (1H, d, J=2.8 Hz), 8.36 (1H, t, J=5.6 Hz), 11.06 (1H, s).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customto give as pale-brown crystals
  6. customirradiation
  7. customin a sealed reaction container at 180° C. for 40 min
  8. concentrationThe reaction mixture was concentrated
  9. filtrationthe precipitated crystals were collected by filtration
  10. washwashed with ethanol

Sources & evidence

ORD record
ord-d156a5b4311940a49b3df1cb2ca43333
Source dataset
uspto-grants-2012_02
Patent number
US08124617B2

Reaction notes

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