Nitrogen → N-[(5-methoxy-1,2,4-triazin-6-yl)methyl]-3-oxocyclobutanecarboxamide

HRID 449018Notes

Reaction equation

HRID 449018 reaction equation
N#N.[CH3:3][O:4][C:5]1[N:6]=[CH:7][N:8]=[N:9][C:10]=1[CH2:11][NH2:12].[O:13]=[C:14]1[CH2:17][CH:16]([C:18](ON2C(=O)CCC2=O)=[O:19])[CH2:15]1.C(=O)([O-])[O-].[Na+].[Na+]>O.[Cl-].[Na+].O.C1COCC1>[CH3:3][O:4][C:5]1[N:6]=[CH:7][N:8]=[N:9][C:10]=1[CH2:11][NH:12][C:18]([CH:16]1[CH2:17][C:14](=[O:13])[CH2:15]1)=[O:19]

Participants

8

Reactant 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 552905845-Methoxy-1,2,4-triazine-6-methanamineHCID 591330492,5-Dioxopyrrolidin-1-yl 3-oxocyclobutanecarboxylate

Product 1

HCID 66915404N-[(5-methoxy-1,2,4-triazin-6-yl)methyl]-3-oxocyclobutanecarboxamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A flask filled with N2 was charged with 1-(5-methoxy-1,2,4-triazin-6-yl)methylamine (3.0 g, 0.021 mol), 1-{[(3-oxocyclobutyl)carbonyl]oxy}pyrrolidine-2,5-dione (5.0 g, 0.024 mol) and THF (50 mL). Sodium carbonate (20 g, 0.2 mol) dissolved in water was added to the reaction mixture slowly at 0° C. The reaction was then stirred at rt for 3 h. The reaction mixture was then concentrated under reduced pressure to give a residue. To this residue brine (500 mL) was added and the mixture was extracted with EtOAc (100 mL×3). The organics were combined, dried (Na2SO4) and concentrated under reduced pressure to give a crude residue, which was then purified by flash chromatography on silica gel using hexanes:EtOAc (2:1) as the eluent. 1H NMR (400 MHz, Chloroform-d) δ 3.12-3.33 (m, 3H), 3.44-3.58 (m, 2H), 4.11 (s, 3H), 4.75 (d, J=4.80 Hz, 2H), 7.11 (br. s., 1H), 9.08 (s, 1H).

Workup

  1. additionwas added to the reaction mixture slowly at 0° C
  2. concentrationThe reaction mixture was then concentrated under reduced pressure
  3. customto give a residue
  4. extractionthe mixture was extracted with EtOAc (100 mL×3)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9833c93bde1a41fd8da60ec2f79157d2
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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