Diisopropylethylamine → 2-methoxy-2-methyl-N-(5-phenylethynyl-pyridin-2-yl)-propionamide

HRID 40542Notes

Reaction equation

HRID 40542 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[CH:10]=[CH:11][C:12]([NH2:15])=[N:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:16][O:17][C:18]([CH3:23])([CH3:22])[C:19](O)=[O:20].F[B-](F)(F)F.BrC1C=CC=C[N+]=1CC.CCN(C(C)C)C(C)C>ClCCl>[CH3:16][O:17][C:18]([CH3:23])([CH3:22])[C:19]([NH:15][C:12]1[CH:11]=[CH:10][C:9]([C:8]#[C:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:14][N:13]=1)=[O:20]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 27363002-Bromo-1-ethylpyridinium tetrafluoroborateHCID 98554652-methoxy-2-methylpropanoic acidHCID 468541905-Phenylethynyl-pyridin-2-ylamine

Product 1

HCID 715483422-methoxy-2-methyl-N-(5-phenylethynyl-pyridin-2-yl)-propionamideYield 46.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(100 mg, 0.515 mmol) 5-Phenylethynyl-pyridin-2-ylamine (Example 1, step 1) was dissolved in dichloromethane (5 ml) and 2-methoxy-2-methylpropionic acid (91 mg, 0.77 mmol, 1.5 equiv.), 2-bromo-1-ethyl pyridinium tetrafluoroborate (CAS 878-23-9) (211 mg, 0.77 mmol, 1.5 equiv.) and Hunig's Base (0.26 ml, 1.54 mmol, 3 equiv.) were added. The mixture was stirred for 14 hours at room temperature. The reaction mixture was extracted with saturated Na2CO3 solution and dichloromethane. The organic layer was dried over sodium sulfate and evaporated to dryness. The crude product was purified by prep HPLC to afford the desired 2-methoxy-2-methyl-N-(5-phenylethynyl-pyridin-2-yl)-propionamide (70 mg, 46% yield) was obtained as a yellow oil, MS: m/e=295.2 (M+H+).

Workup

  1. extractionThe reaction mixture was extracted with saturated Na2CO3 solution and dichloromethane
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated to dryness
  4. customThe crude product was purified by prep HPLC

Sources & evidence

ORD record
ord-98a07b23b5e94b878356f0ee97fa61bd
Source dataset
uspto-grants-2013_09
Patent number
US08530472B2

Reaction notes

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