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Hydrochloric Acid → 5-(4-chlorophenyl)-N-(2-cyclohexyl-2-oxoethyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide

HRID 254835
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HRID 254835 반응식
[CH:1]1([C:7](=[O:17])[CH2:8][NH:9][C:10](=[O:16])OC(C)(C)C)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.Cl.NCC(C1CCCCC1)=O.[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[N:41]([C:42]3[CH:47]=[CH:46][C:45]([Cl:48])=[CH:44][C:43]=3[Cl:49])[N:40]=[C:39](C(O)=O)[C:38]=2[CH3:53])=[CH:33][CH:32]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>C(Cl)Cl.O1CCOCC1.CN(C=O)C>[Cl:30][C:31]1[CH:32]=[CH:33][C:34]([C:37]2[N:41]([C:42]3[CH:47]=[CH:46][C:45]([Cl:48])=[CH:44][C:43]=3[Cl:49])[N:40]=[C:39]([C:10]([NH:9][CH2:8][C:7]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)=[O:17])=[O:16])[C:38]=2[CH3:53])=[CH:35][CH:36]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

11

반응물 7

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 15194215-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acidHCID 222816062-Amino-1-cyclohexylethan-1-one hydrochloride
HCID 58430272
tert-butyl N-(2-cyclohexyl-2-oxoethyl)carbamate

생성물 1

HCID 668447715-(4-chlorophenyl)-N-(2-cyclohexyl-2-oxoethyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide수율 49%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

실험 절차

To a tert-butyl 2-cyclohexyl-2-oxoethylcarbamate (228 mg, 0.946 mmol) in DCM (5 mL) was added 4M HCl in 1,4-dioxane (5 mL) at room temperature. The reaction continued for an hour at room temperature. The volatiles were removed under vacuum. To the residue (2-amino-1-cyclohexylethanone hydrochloric acid), 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid (361 mg, 0.946 mmol), EDCI (272 mg, 1.429 mmol), HOBt (192 mg, 1.429 mmol) in DMF (9 mL) was added NMM (1.0 mL, 9.46 mmol) at room temperature. The reaction mixture was stirred at room temperature overnight. The residue was purified by reverse-phase prep HPLC to afford the title compound (232 mg, 49%).

후처리

  1. waitThe reaction continued for an hour at room temperature
  2. customThe volatiles were removed under vacuum
  3. customThe residue was purified by reverse-phase prep HPLC

출처 및 근거

ORD 기록
ord-295dea42246b4d318587c133dab8c614
출처 데이터셋
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07875647B2

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