Triethylamine → HCID 14390499, compound

HRID 2351597Notes

Reaction equation

HRID 2351597 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][NH:6][C:7]1[C:12]([NH2:13])=[CH:11][CH:10]=[CH:9][N:8]=1)[CH3:2].C(OC(=O)CNC1C([N+]([O-])=O)=CC=CN=1)C.C(N(CC)CC)C.[Br:38][C:39]1[CH:47]=[CH:46][C:42]([C:43](Cl)=[O:44])=[CH:41][CH:40]=1>O1CCCC1.[Pd].C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:14])[CH2:5][NH:6][C:7]1[C:12]([NH:13][C:43](=[O:44])[C:42]2[CH:46]=[CH:47][C:39]([Br:38])=[CH:40][CH:41]=2)=[CH:11][CH:10]=[CH:9][N:8]=1)[CH3:2]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 685154-Bromobenzoyl chlorideHCID 14062544Ethyl 2-[(3-nitropyridin-2-YL)amino]acetateHCID 14390203Ethyl 2-(3-aminopyridin-2-ylamino)acetate

Product 1

HCID 14390499HCID 14390499, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred and chilled (10°-20° C.) solution of N-(3-amino-2-pyridinyl)glycine ethyl ester (14.7 g, 0.075 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 8.1 g, 0.080 mole), and tetrahydrofuran (150 ml) was added (rapid drop) 4-bromobenzoyl chloride (6.9 g, 0.077 mole), followed by 100 ml of methylene chloride. The reaction mixture was stirred at room temperature for 2 hr and was filtered. The filtrate was concentrated in vacuo and the residue combined with the filter cake. The combined mixture was twice suspended in water and filtered. The filter cake was recrystallized from ethanol, giving 22.7 g of crystals (80%). Recrystallization of a 1.6-g samples from ethanol gave 1.5 g of white flocculent solid, mp 153°-154° C.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 2 hr
  2. filtrationwas filtered
  3. concentrationThe filtrate was concentrated in vacuo
  4. filtrationfiltered
  5. customThe filter cake was recrystallized from ethanol

Sources & evidence

ORD record
ord-340b45d92bf9425bb9e3f8caba44146d
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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