Triethylamine → HCID 14390498, compound

HRID 2072916Notes

Reaction equation

HRID 2072916 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].[CH2:11]([O:13][C:14](=[O:24])[CH2:15][NH:16][C:17]1[C:22]([NH2:23])=[CH:21][CH:20]=[CH:19][N:18]=1)[CH3:12].C(OC(=O)CNC1C([N+]([O-])=O)=CC=CN=1)C.C(N(CC)CC)C>O1CCCC1.[Pd]>[CH2:11]([O:13][C:14](=[O:24])[CH2:15][NH:16][C:17]1[C:22]([NH:23][C:5](=[O:6])[C:4]2[CH:8]=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=2)=[CH:21][CH:20]=[CH:19][N:18]=1)[CH3:12]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 743763-Fluorobenzoyl chlorideHCID 14062544Ethyl 2-[(3-nitropyridin-2-YL)amino]acetateHCID 14390203Ethyl 2-(3-aminopyridin-2-ylamino)acetate

Product 1

HCID 14390498HCID 14390498, compoundYield 6.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen atmosphere, 3-fluorobenzoyl chloride (12.9 g, 0.0816 mole) was added dropwise to a stirred and chilled (10°-15° C.) mixture of N-(3-amino-2-pyridinyl)glycine ethyl ester (0.0816 mole) [freshly prepared by the hydrogenation of a solution of N-(3-nitro-2-pyridinyl)glycine ethyl ester in tetrahydrofuran over 5% palladium on carbon at room temperature], triethylamine (8.3 g, 0.0816 mole), anhydrous tetrahydrofuran (200 ml), and powdered molecular sieves. The reaction mixture was stirred at room temperature for 1 hour and was filtered. The filtrate was concentrated in vacuo and the residual solid triturated in isopropyl ether-isopropyl alcohol, giving 24.2 g (94%). Recrystallization of a 2.0-g sample gave 1.72 g of a white powder, mp 134°-135° C.

Workup

  1. temperaturechilled
  2. stirringThe reaction mixture was stirred at room temperature for 1 hour
  3. filtrationwas filtered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residual solid triturated in isopropyl ether-isopropyl alcohol
  6. customgiving 24.2 g (94%)
  7. customRecrystallization of a 2.0-g sample

Sources & evidence

ORD record
ord-b6bb195fcf234cf3a52d0ab2e9483cca
Source dataset
uspto-grants-1990_04
Patent number
US04914109

Reaction notes

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