2,4,6-Trimethylpyridine → HCID 67981371, compound

HRID 2174320Notes

Reaction equation

HRID 2174320 reaction equation
O[C:2]([C:4](F)(F)F)=[O:3].NCC[N:11]1[C:15](=[O:16])C=[CH:13][C:12]1=[O:17].[N:18]1C(C)=CC(C)=CC=1C.CN1[C:32](=[O:33])CCC1>O>[NH2:18][O:33][CH2:32][C:2]([C:4]1[C:15]([NH:11][C:12](=[O:17])[CH:13]=1)=[O:16])=[O:3]

Participants

5

Reactant 3

HCID 79532,4,6-TrimethylpyridineHCID 13387N-methyl-2-pyrrolidoneHCID 16212752Trifluoroacetic acid--1-(2-aminoethyl)-1H-pyrrole-2,5-dione (1/1)

Product 1

HCID 67981371HCID 67981371, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-(2-Aminoethyl)maleimide TFA salt (51 mg, 0.20 mmol) and Eei-AOAc-OSu (77 mg, 0.30 mmol) were dissolved in NMP (2 mL). Sym.-collidine (80 μL, 0.6 mmol) was added and the reaction mixture stiffed for 70 min. The reaction mixture was diluted with water (7 mL) and the product, eei-aminooxyacetyl-maleimide, purified by semi-preparative HPLC. Purification using semi-preparative HPLC (gradient: 15-30% B over 40 min where A=water/0.1% acetic acid and B=ACN) affording 43 mg (75%) pure Eei-aminooxyacetyl-maleimide. The purified material, eei-aminooxyacetyl-maleimide, was characterised by LC-MS (gradient: 10-40% B over 5): tR: 1.93 min. found m/z: 284.1, expected MH+: 284.1

Workup

  1. customthe product, eei-aminooxyacetyl-maleimide, purified by semi-preparative HPLC
  2. customPurification

Sources & evidence

ORD record
ord-b508657652f948408de7561a63840afb
Source dataset
uspto-grants-2015_06
Patent number
US09061080B2

Reaction notes

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