Diisopropylethylamine → HCID 66989303, compound

HRID 2407746Notes

Reaction equation

HRID 2407746 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([O:10][CH2:11][CH3:12])[N:5]=[C:4]([C:13]([OH:15])=O)[CH:3]=1.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.Cl.Cl.[N:50]1[CH:55]=[CH:54][CH:53]=[CH:52][C:51]=1[C:56]1[S:60][C:59]([S:61]([N:64]2[CH2:69][CH2:68][CH:67]([CH2:70][NH2:71])[CH2:66][CH2:65]2)(=[O:63])=[O:62])=[CH:58][CH:57]=1>CN(C)C=O>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([O:10][CH2:11][CH3:12])[N:5]=[C:4]([C:13]([NH:71][CH2:70][CH:67]2[CH2:66][CH2:65][N:64]([S:61]([C:59]3[S:60][C:56]([C:51]4[CH:52]=[CH:53][CH:54]=[CH:55][N:50]=4)=[CH:57][CH:58]=3)(=[O:63])=[O:62])[CH2:69][CH2:68]2)=[O:15])[CH:3]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 118464604-Amino-5-cyano-6-ethoxypicolinic acidHCID 66989693HCID 66989693, compound

Product 1

HCID 66989303HCID 66989303, compoundYield 42.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-amino-5-cyano-6-ethoxypicolinic acid (0.038 g) in N,N-dimethylformamide (2 mL) was treated with 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (0.039 g), 1-hyroxybenzotriazole hydrate (0.031 g), followed by diisopropylethylamine (0.096 mL) at room temperature. After stirring for 15 minutes, the compound prepared in Example 244 (0.079 g) was added. Stirring was continued overnight, and the resulting mixture was washed with water, and the product extracted with ethyl acetate. The organic layer was separated, filtered, evaporated in vacuo and the residue triturated in 1:1 hexane-diethyl ether. The precipitated solids were collected by filtration to provide the title compound (0.041 g) having the following physical data.

Workup

  1. stirringStirring
  2. waitwas continued overnight
  3. washthe resulting mixture was washed with water
  4. extractionthe product extracted with ethyl acetate
  5. customThe organic layer was separated
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customthe residue triturated in 1:1 hexane-diethyl ether
  9. filtrationThe precipitated solids were collected by filtration

Sources & evidence

ORD record
ord-1d777d9df14840549e646659dbb5db2f
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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