3,4-Diaminopyridine → HCID 178420318, compound

HRID 2367376Notes

Reaction equation

HRID 2367376 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH2:7])=[C:3]([NH2:8])[CH:2]=1.Cl.[CH2:10]([N:17]1[CH2:22][CH2:21][O:20][CH:19]([C:23](O)=O)[CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[NH4+].[OH-]>O>[C:11]1([CH2:10][N:17]2[CH2:22][CH2:21][O:20][CH:19]([C:23]3[NH:7][C:4]4[CH:5]=[CH:6][N:1]=[CH:2][C:3]=4[N:8]=3)[CH2:18]2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 59183,4-DiaminopyridineHCID 14923Ammonium HydroxideHCID 27763524-Benzylmorpholine-2-carboxylic acid hydrochloride

Product 1

HCID 178420318HCID 178420318, compoundYield 21.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3,4-pyridinediamine (1.7 g, 15.58 mmol), 4-benzylmorpholine-2-carboxylic acid hydrochloride (4.82 g, 18.69 mmol) and polyphosphoric acid (40 mL, 15.58 mmol) was refluxed for 12 hours. Then water (70 mL) and NH4OH were added thereto, and the resulting mixture was extracted with CH2Cl2 (10% CH3OH) (3×80 mL). The combined organic solution was washed with brine (2×100 mL), dried, and evaporated in vacuo to afford the title compound (1.0 g). LC-MS (ES) m/z=295 [M+H]+.

Workup

  1. temperaturewas refluxed for 12 hours
  2. extractionthe resulting mixture was extracted with CH2Cl2 (10% CH3OH) (3×80 mL)
  3. washThe combined organic solution was washed with brine (2×100 mL)
  4. customdried
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-4fd7963af4c24ea0bc2d290adca3a42c
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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