Triethylamine → HCID 9851664, compound

HRID 2229195Notes

Reaction equation

HRID 2229195 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:25])=[C:6]([CH2:8][C:9]2[N:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]3=[N:11][C:10]=2[CH2:18][NH:19][CH2:20][CH2:21][CH:22]([CH3:24])[CH3:23])[CH:7]=1.C(N(CC)CC)C.[Cl:33][C:34]1[C:42]([O:43][CH3:44])=[C:41]([O:45][CH3:46])[CH:40]=[CH:39][C:35]=1[C:36](Cl)=[O:37]>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:25])=[C:6]([CH2:8][C:9]2[N:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]3=[N:11][C:10]=2[CH2:18][N:19]([CH2:20][CH2:21][CH:22]([CH3:23])[CH3:24])[C:36]([C:35]2[CH:39]=[CH:40][C:41]([O:45][CH3:46])=[C:42]([O:43][CH3:44])[C:34]=2[Cl:33])=[O:37])[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11481734HCID 11481734, compoundHCID 22091465HCID 22091465, compound

Product 1

HCID 9851664HCID 9851664, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

A solution of 90 mg (0.25 mmol) ({3-[(5-bromo-2-hydroxyphenyl)methyl](imidazolo[1,2-a]pyridin-2-yl)}methyl)(3-methylbutyl)amine in 4 mL dichloromethane at 0° C. is treated with triethylamine 50 mg (0.50 mmol) and then 2-chloro-3,4-dimethoxybenzoylchloride 110 mg (0.50 mmol). The solution is stirred overnight and the volatiles removed by rotary evaporation. The residue is dissolved in 4 mL methanol and treated with 2 mL 1M sodium hydroxide. The solution is heated to 45° C. for 1 hr and the volatiles removed by rotary evaporation. The mixture is acidified with 1M hydrochloric acid, extracted with 3×5 mL ethyl acetate and the combined extracts washed with 5 mL brine. The combined extract is dried over anhydrous MgSO4 and the solvent removed in vacuo to yield 120 mg (80%) N-({3-[(5-bromo-2-hydroxyphenyl)methyl](imidazolo[1,2-a]pyridin-2-yl)}methyl)(2-chloro-3,4-dimethoxyphenyl)-N-(3-methylbutyl)carboxamide. Mass Spec m/z (M++1) 602.

Workup

  1. customthe volatiles removed by rotary evaporation
  2. dissolutionThe residue is dissolved in 4 mL methanol
  3. additiontreated with 2 mL 1M sodium hydroxide
  4. customthe volatiles removed by rotary evaporation
  5. extractionextracted with 3×5 mL ethyl acetate
  6. washthe combined extracts washed with 5 mL brine
  7. extractionThe combined extract
  8. dry with materialis dried over anhydrous MgSO4
  9. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-294795e5a1264c83b20cb5ba4aef609c
Source dataset
uspto-grants-2002_07
Patent number
US06420365B1

Reaction notes

Loading…