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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
ノート
印刷プレビュー

反応式

HRID 254835 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

11

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-295dea42246b4d318587c133dab8c614
出典データセット
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07875647B2

反応ノート

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