Betahistine → HCID 9975437, compound

HRID 1755577Notes

Reaction equation

HRID 1755577 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.C[NH:32][CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=1>C1COCC1>[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]([NH:32][CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=1)=[O:16])[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 2366BetahistineHCID 40634TroloxHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 9975437HCID 9975437, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (500 mg, 2.0 mmol) in 10 mL THF was treated with 356 mg CDI (2.2 mmol). After 1 h, 366 mg 2-(2-methylaminoethyl)pyridine (3.0 mmol) in 10 mL THF was added over 1 h and stirred overnight. The solution was concentrated, dissolved into 70 mL CH2Cl2, extracted once with 1.0 M NaHCO3. The aqueous phase was then back extracted 2×25 mL CH2Cl2 and the combined organics washed with 2×25 mL saturated NaCl and dried over Na2SO4. The solution was concentrated and purified by flash chromatography to give 6-hydroxy-2,5,7,8-tetramethyl-N-(2-(pyridin-2-yl)ethyl)chroman-2-carboxamide.

Workup

  1. concentrationThe solution was concentrated
  2. dissolutiondissolved into 70 mL CH2Cl2
  3. extractionextracted once with 1.0 M NaHCO3
  4. extractionThe aqueous phase was then back extracted 2×25 mL CH2Cl2
  5. washthe combined organics washed with 2×25 mL saturated NaCl
  6. dry with materialdried over Na2SO4
  7. concentrationThe solution was concentrated
  8. custompurified by flash chromatography

Sources & evidence

ORD record
ord-889f731e2dab4bf3b7a059f64b9d7a68
Source dataset
uspto-grants-2015_10
Patent number
US09169196B2

Reaction notes

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