Carbonic acid-guanidine (1:1) → HCID 70873430, compound

HRID 925412Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:25])=[C:6]([N:8]2[C:12]([C:13]([O:15]CC)=[O:14])=[CH:11][C:10]([C:18](=O)/[CH:19]=[CH:20]/N(C)C)=[N:9]2)[CH:7]=1.C(=O)(O)O.[NH2:30][C:31]([NH2:33])=[NH:32]>CN(C=O)C>[NH2:32][C:31]1[N:33]=[C:18]([C:10]2[CH:11]=[C:12]([C:13]([OH:15])=[O:14])[N:8]([C:6]3[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=3[CH3:25])[N:9]=2)[CH:19]=[CH:20][N:30]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a mixture of ethyl 1-(5-chloro-2-methylphenyl)-3-[(2E)-3-(dimethylamino)prop-2-enoyl]-1H-pyrazole-5-carboxylate (260 mg, 0.72 mmol) in DMF (4 mL), guanidine carbonate (130 mg, 0.72 mmol) was added. The mixture was heated at 110° C. overnight under efficient stirring. The resulting mixture was concentrated, dissolved in MeOH (0.5 mL) and THF (0.5 mL) and treated with NaOH 1N (0.5 mL). After 1 h the mixture was concentrated, dissolved in water and washed with AcOEt. To the aqueous phase cooled to 5° C., a saturated solution of citric acid was added under stirring. The resulting precipitate was collected by filtration to give the title compound (156 mg, 65%).

Workup

additionwas added
concentrationThe resulting mixture was concentrated
dissolutiondissolved in MeOH (0.5 mL)
additionTHF (0.5 mL) and treated with NaOH 1N (0.5 mL)
concentrationAfter 1 h the mixture was concentrated
dissolutiondissolved in water
washwashed with AcOEt
temperatureTo the aqueous phase cooled to 5° C.
additiona saturated solution of citric acid was added
filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record: ord-06b454ae70bc40549b1c8d54a4598ec2
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284298B2

Reaction notes

Loading…