Beta-Alanine → HCID 86636691, compound

HRID 409364Notes

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.[F:19][C:20]([F:36])([F:35])[O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[S:32][C:31]([CH:33]=O)=[CH:30][CH:29]=2)=[CH:24][CH:23]=1.NCCC(O)=O.CO.C(Cl)Cl>C(O)(=O)C>[F:36][C:20]([F:19])([F:35])[O:21][C:22]1[CH:23]=[CH:24][C:25]([C:28]2[S:32][C:31]([CH:33]=[C:3]3[C:2](=[O:1])[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:5](=[S:18])[NH:4]3)=[CH:30][CH:29]=2)=[CH:26][CH:27]=1

Participants

Conditions

Temperature: 170 °C

Procedure

To a mixture of 2-(5-oxo-2-thioxoimidazolidin-1-yl)-3-phenylpropanoic acid (0.031 g, 0.117 mmol) and 5-(4-trifluoromethoxy-phenyl)thiophene-2-carbaldehyde (0.030 g, 0.117 mmol) in acetic acid 5 mL is added β-alanine (1.042 mg, 0.012 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 (0.035 g, 0.069 mmol, red solid) is obtained by column chromatography using MeOH/DCM, 2-7% ration solvent system. 1H-NMR (CD3OD/300 MHz): 7.91 (m, 2H), 7.32 (d, J=9.0 Hz, 2H), 7.14 (m, 5H), 7.02 (m, 2H), 6.47 (s, 1H), 5.64 (dd, J=11.1, 5.4 Hz, 11H), 3.70 (dd, J=14.1, 12.6 Hz, 1H), 3.53 (dd, J=14.1, 5.1 Hz, 1H). MS (ES−, m/z): 501.4 (M−, 100.0).

Workup

customThe resulting reaction mixture
temperatureis cooled down
customthe solvent is removed
customThe pure product (0.035 g, 0.069 mmol, red solid) is obtained by column chromatography

Sources & evidence

ORD record: ord-ee85277a7edd4c5a99322da8e9697d0c
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759384B2

Reaction notes

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