Beta-Alanine → HCID 57994046, compound

HRID 409361Notes

Reaction equation

HRID 409361 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]2S[C:29]([CH:31]=O)=[CH:28][CH:27]=2)=[CH:22][CH:21]=1.NCCC(O)=[O:37].CO.C(Cl)Cl>C(O)(=O)C>[Br:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[O:37][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][CH:21]=1

Participants

6

Reactant 4

HCID 239Beta-AlanineHCID 35780565-(4-bromophenyl)thiophene-2-carbaldehydeHCID 21226129Dichloromethane methanolHCID 57994057HCID 57994057, compound

Product 1

HCID 57994046HCID 57994046, 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 (0.053 g, 0.199 mmol) and 5-(4-bromophenyl)thiophene-2-carbaldehyde (0.050 g, 0.199 mmol) in acetic acid 5 mL is added β-alanine (1.8 mg, 0.020 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 (0.060 g, 0.120 mmol, red solid) is obtained by column chromatography using MeOH/DCM, 2-7% ration solvent system. 1H-NMR (CD3OD/300 MHz): 7.83 (dm, J=9.0 Hz, 2H), 7.44 (dm, J=9.3 Hz, 2H), 7.17 (m, 5H), 7.03 (s, 2H), 6.47 (s, 1H), 5.64 (d, J=8.7 Hz, 1H), 3.69 (m, 1H), 3.49 (m, 1H). MS (ES−, m/z): 495.2 (M−, 80.0).

Workup

  1. customThe resulting reaction mixture
  2. temperatureis cooled down
  3. customthe solvent is removed
  4. customThe pure product (0.060 g, 0.120 mmol, red solid) is obtained by column chromatography

Sources & evidence

ORD record
ord-dda2fc13f046444b8f9e49313082ab67
Source dataset
uspto-grants-2014_06
Patent number
US08759384B2

Reaction notes

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