Beta-Alanine → HCID 57994056, compound

HRID 409363Notes

Reaction equation

HRID 409363 reaction equation
[O:1]=[C:2]1[N:6]([CH:7]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]([OH:10])=[O:9])[C:5](=[S:18])[NH:4][CH2:3]1.[Br:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[S:30][C:29]([CH:31]=O)=[CH:28][CH:27]=2)=[CH:22][C:21]=1[Cl:33].NCCC(O)=O.CO.C(Cl)Cl>C(O)(=O)C>[Br:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[S:30][C:29](/[CH:31]=[C:3]3/[NH:4][C:5](=[S:18])[N:6]([CH:7]([CH2:11][C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)[C:8]([OH:10])=[O:9])[C:2]/3=[O:1])=[CH:28][CH:27]=2)=[CH:22][C:21]=1[Cl:33]

Participants

6

Reactant 4

HCID 239Beta-AlanineHCID 21226129Dichloromethane methanolHCID 57994057HCID 57994057, compoundHCID 57994060HCID 57994060, compound

Product 1

HCID 57994056HCID 57994056, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
170 °C

Procedure

To a mixture of 2-(5-oxo-2-thioxoimidazolidin-1-yl)-3-phenylpropanoic acid (0.044 g, 0.175 mmol) and 5-(4-bromo-3-chloro-phenyl)thiophene-2-carbaldehyde (0.050 g, 0.166 mmol) in acetic acid 5 mL is added β-alanine (1.6 mg, 0.01 r8 mmol) and heat to 170° C. for 30 min under microwave irradiation. The resulting reaction mixture is cooled down and the solvent is removed. The pure product (0.075 g, 0.141 mmol, red solid) is obtained by column chromatography using MeOH/DCM, 2-7% ration solvent system. 1H-NMR (CDCl3/300 MHz): 9.88 (br, 1H), 8.92 (br, 1H), 7.65 (m, 2H), 7.31 (m, 8H), 6.85 (s, 1H), 5.76 (dd, J=11.1, 5.4 Hz, 1H), 3.70 (m, 2H). MS (ES−, m/z): 545.2 (M−, 100.0).

Workup

  1. customThe resulting reaction mixture
  2. temperatureis cooled down
  3. customthe solvent is removed
  4. customThe pure product (0.075 g, 0.141 mmol, red solid) is obtained by column chromatography

Sources & evidence

ORD record
ord-e5eab9dceb214be2964d79efb9c587ea
Source dataset
uspto-grants-2014_06
Patent number
US08759384B2

Reaction notes

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