Pyridine → phenyl 1-(4-chlorophenyl)-3-methyl-1H-pyrazol-5-yl-carbamate

HRID 1864659Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([NH2:13])=[CH:11][C:10]([CH3:14])=[N:9]2)=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:22]([O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:23]>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([NH:13][C:22](=[O:23])[O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:11][C:10]([CH3:14])=[N:9]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

1-(4-chlorophenyl)-3-methyl-1H-pyrazol-5-amine (100 mg, 0.48 mmol) was dissolved in dry THF (6 mL). Pyridine (51 μL, 0.62 mmol) was added and the solution was cooled in an ice bath under nitrogen surpressure. Phenyl chloroformate (73 μL, 0.58 mmol) was slowly added and the mixture was stirred at 0° C. during 5 min and at room temperature during 1.5 h. The mixture was then diluted in EtOAc (10 mL) and the salts remaining were filtrated off. The filtrate was concentrated under reduced pressure. The resulting white solid was washed with a little amount of cold EtOAc and water to afford the title compound (41 mg, 26%) as a white solid. 1H-NMR (δ, ppm, DMSO-d6): 2.22 (s, 3H, CH3), 6.28 (s, 1H, HPyz,4), 7.11-7.60 (m, 9H, Harom), 10.14 (bs, 1H, NH). LC-MS (m/z): 328 (M+H, 100).

Workup

temperaturethe solution was cooled in an ice bath under nitrogen surpressure
filtrationthe salts remaining were filtrated off
concentrationThe filtrate was concentrated under reduced pressure
washThe resulting white solid was washed with a little amount of cold EtOAc and water

Sources & evidence

ORD record: ord-faeac165ae834c989671081f98697087
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625922B2

Reaction notes

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