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Beta-Alanine → HCID 75039751, compound

HRID 409353
Notes
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Reaction equation

HRID 409353 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.[Cl: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][CH:21]=1.NCCC(O)=O.CO.C(Cl)Cl>C(O)(=O)C>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]2[S:30][C:29]([CH:31]=[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:28][CH:27]=2)=[CH:24][CH:25]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 239Beta-AlanineHCID 27635855-(4-Chlorophenyl)thiophene-2-carbaldehydeHCID 21226129Dichloromethane methanolHCID 57994057HCID 57994057, compound

Product 1

HCID 75039751HCID 75039751, compound

Reagents, catalysts & solvents 1

HCID 176
Acetic Acid
Solvent

Conditions

Temperature
170 °C

Procedure

To a mixture of 2-(5-oxo-2-thioxoimidazolidin-1-yl)-3-phenylpropanoic acid (0.080 g, 0.304 mmol) and 5-(4-chorophenyl)thiophene-2-carbaldehyde (0.068 g, 0.304 mmol) in acetic acid 5 mL is added β-alanine (2.7 mg, 0.030 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 (0.110 g, 0.235 mmol, red solid) is obtained by column chromatography using MeOH/DCM, 2-7% ration solvent system. 1H-NMR (CD3OD/300 MHz): 7.66 (dd, J=8.7, 1.5 Hz, 2H), 7.50 (dm, J=12.6 Hz, 2H), 7.40 (d, J=8.4 Hz, 2H), 7.18 (m, 5H), 6.69 (s, 1H), 5.65 (dd, J=12.0, 4.5 Hz, 1H), 3.68 (dd, J=13.8, 12.0 Hz, 1H), 3.51 (dd, J=14.4, 4.5 Hz, 1H). MS (ES+, m/z): 469.5 (M++1, 30.0).

Workup

  1. customThe resulting reaction mixture
  2. temperatureis cooled down
  3. customthe solvent is removed
  4. customThe pure product (0.110 g, 0.235 mmol, red solid) is obtained by column chromatography

Sources & evidence

ORD record
ord-e0f5ad537ea94a7f9316fb9c38f5d4a8
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08759384B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes