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Triethylamine → ethyl 4-((4-chlorophenyl)((3,7-dimethylbenzo[d]isoxazol-5-yl)amino)-methyl)-1-(2,4-dimethoxypyrimidin-5-yl)-5-isopropyl-1H-pyrazole-3-carboxylate

HRID 873888
ノート
印刷プレビュー

反応式

HRID 873888 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[C:9]2[C:10]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[N:11][N:12]([C:17]3[C:18]([O:25][CH3:26])=[N:19][C:20]([O:23][CH3:24])=[N:21][CH:22]=3)[C:13]=2[CH:14]([CH3:16])[CH3:15])=[CH:4][CH:3]=1.C(N(CC)CC)C.O(S(C)(=O)=O)S(C)(=O)=O.[CH3:49][C:50]1[C:54]2[CH:55]=[C:56]([NH2:60])[CH:57]=[C:58]([CH3:59])[C:53]=2[O:52][N:51]=1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([NH:60][C:56]2[CH:57]=[C:58]([CH3:59])[C:53]3[O:52][N:51]=[C:50]([CH3:49])[C:54]=3[CH:55]=2)[C:9]2[C:10]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[N:11][N:12]([C:17]3[C:18]([O:25][CH3:26])=[N:19][C:20]([O:23][CH3:24])=[N:21][CH:22]=3)[C:13]=2[CH:14]([CH3:16])[CH3:15])=[CH:6][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8471TriethylamineHCID 81560Methanesulfonic anhydrideHCID 89602026ethyl 4-((4-chlorophenyl)(hydroxy)methyl)-1-(2,4-dimethoxypyrimidin-5-yl)-5-isopropyl-1H-pyrazole-3-carboxylateHCID 1171101573,7-Dimethylbenzo[d]isoxazol-5-amine

生成物 1

HCID 117702629ethyl 4-((4-chlorophenyl)((3,7-dimethylbenzo[d]isoxazol-5-yl)amino)-methyl)-1-(2,4-dimethoxypyrimidin-5-yl)-5-isopropyl-1H-pyrazole-3-carboxylate
収率 63%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of ethyl 4-((4-chlorophenyl)(hydroxy)methyl)-1-(2,4-dimethoxypyrimidin-5-yl)-5-isopropyl-1H-pyrazole-3-carboxylate (Step 46.11) (500 mg, 1.085 mmol) and triethylamine (0.756 mL, 5.42 mmol) in CH2Cl2 (10 mL) cooled down to 0° C. was added Ms2O (378 mg, 2.170 mmol) and the reaction was stirred for 1 hr at this temperature. 3,7-dimethylbenzo[d]isoxazol-5-amine (Step 46.6) (194 mg, 1.193 mmol) was added and the reaction mixture was allowed to warm up to RT and stir for 1 hr. The reaction was quenched with aq. NaH2PO4 solution and extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (hexane/EtOAc 10-100%) to afford the title product (460 mg, 0.684 mmol, 63% yield) as yellow amorphous solid. tR: 1.38 min (LC-MS 2); ESI-MS: 605 [M+H]+ (LC-MS 2); Rf=0.25 (hexane/EtOAc 1:1).

後処理

  1. stirringstir for 1 hr
  2. customThe reaction was quenched with aq. NaH2PO4 solution
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by silica gel column chromatography (hexane/EtOAc 10-100%)

出典と根拠

ORDレコード
ord-5c42983760424643b9131a66298803b6
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08975417B2

反応ノート

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