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

HRID 1864659노트

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HRID 1864659 반응식
[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

참가 물질

6

반응물 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 1703011H-Pyrazol-5-amine, 1-(4-chlorophenyl)-3-methyl-

생성물 1

HCID 46196893phenyl 1-(4-chlorophenyl)-3-methyl-1H-pyrazol-5-yl-carbamate수율 26.1%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-faeac165ae834c989671081f98697087
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07625922B2

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