Beta-Alanine → HCID 86663515, compound

HRID 2406559Notes

Reaction equation

HRID 2406559 reaction equation
NCCC(O)=O.[Br:7][C:8]1[N:13]=[C:12]([CH:14]=O)[CH:11]=[CH:10][CH:9]=1.[C:16]([CH2:18][C:19]([NH:21][CH:22]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][O:34][CH3:35])=[CH:28][CH:27]=1)[CH2:23][CH2:24][CH3:25])=[O:20])#[N:17]>C(O)C.O.CCOC(C)=O.CCCCCC>[Br:7][C:8]1[N:13]=[C:12](/[CH:14]=[C:18](\[C:16]#[N:17])/[C:19]([NH:21][CH:22]([C:26]2[CH:27]=[CH:28][C:29]([O:32][CH2:33][O:34][CH3:35])=[CH:30][CH:31]=2)[CH2:23][CH2:24][CH3:25])=[O:20])[CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 239Beta-AlanineHCID 27570096-Bromopyridine-2-carbaldehydeHCID 66822001HCID 66822001, compound

Product 1

HCID 86663515HCID 86663515, compoundYield 186.8%

Reagents, catalysts & solvents 2

HCID 19096565Water ethanolSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

β-Alanine (1.42 g, 16 mmol) and 6-bromopyridine-2-carboxaldehyde (744 mg, 4 mmol) were added successively to a stirred solution of 2-cyano-N-(1-(4-(methoxymethoxy)phenyl)butyl)acetamide (276 mg, 1.0 mmol) in ethanol/water (28 mL/17 mL) at room temp. After 72 hours TLC (in 25% EtOAc/Hexane) showed a single product and some starting materials. The mixture was partitioned between aqueous sodium bicarbonate and ethyl acetate. The separated organic layer was washed with sat. brine and dried with sodium sulfate and concentrated to give a light amber oil (830 mg) as crude product. The crude material was purified by flash chromatography to afford the title compound as a yellow oil (253 mg) in 57% yield. 1H NMR (500 MHz, CDCl3) δ 7.59 (dd, J=7.9, 7.5 Hz, 1H), 7.52 (d, J=8.0 Hz, 1H), 7.27 (d, J=8.6 Hz, 2H), 7.22 (d, J=7.4 Hz, 1H), 6.96 (d, J=8.6 Hz, 2H), 6.82 (s, 1H), 5.19 (s, 2H), 3.85 (t, J=7.6 Hz, 1H), 3.49 (s, 3H), 1.67 (m, 2H), 1.39 (m, 2H), 0.94 (t, J=7.3 Hz, 3H); Mass spec ES+; m/z=444.0 (m+1) and 466.0 (m+Na+).

Workup

  1. customThe mixture was partitioned between aqueous sodium bicarbonate and ethyl acetate
  2. washThe separated organic layer was washed with sat. brine
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-835fd496674c491c84fc6e612230f6dd
Source dataset
uspto-grants-2014_08
Patent number
US08809377B2

Reaction notes

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