Trolox → HCID 67262909, compound

HRID 1755569Notes

Reaction equation

HRID 1755569 reaction equation
[OH:1][C:2]1[C:3]([CH3:18])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH3:17])([C:14]([OH:16])=O)[CH2:6][CH2:5]2.C1N=CN(C(N2C=NC=C2)=O)C=1.[NH2:31][CH2:32][CH2:33][CH2:34][N:35]1[CH:39]=[CH:38][N:37]=[CH:36]1>C1COCC1>[N:35]1([CH2:34][CH2:33][CH2:32][NH:31][C:14]([C:7]2([CH3:17])[CH2:6][CH2:5][C:4]3[C:9](=[C:10]([CH3:13])[C:11]([CH3:12])=[C:2]([OH:1])[C:3]=3[CH3:18])[O:8]2)=[O:16])[CH:39]=[CH:38][N:37]=[CH:36]1

Participants

5

Reactant 3

HCID 40634TroloxHCID 682631,1'-CarbonyldiimidazoleHCID 787361H-Imidazole-1-propanamine

Product 1

HCID 67262909HCID 67262909, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (500 mg, 2.00 mmol) in 10 mL THF was treated with 358 mg CDI and stirred for 1.25 h at room temperature. To this clear yellow solution was added a solution of 278 mg 1-(3-aminopropyl)imidazole in 10 mL THF over 1 h. The solution was stirred overnight at room temperature, concentrated to a pale brown oil, dissolved into 70 mL CH2Cl2, washed 1×50 mL saturated NaCl, and dried over Na2SO4. The organic layers were concentrated and flashed chromatographed to yield 524 mg of N-(3-(1H-imidazol-1-yl)propyl)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxamide as a white crystalline solid.

Workup

  1. stirringThe solution was stirred overnight at room temperature
  2. concentrationconcentrated to a pale brown oil
  3. dissolutiondissolved into 70 mL CH2Cl2
  4. washwashed 1×50 mL saturated NaCl
  5. dry with materialdried over Na2SO4
  6. concentrationThe organic layers were concentrated
  7. customflashed chromatographed

Sources & evidence

ORD record
ord-fa2d9cb3ef6d4b20af4ad691e250c625
Source dataset
uspto-grants-2015_10
Patent number
US09169196B2

Reaction notes

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