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Ethyl Acetate → 4-{5-[3-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-ureido]-pyridin-2-yl}-piperazine-1-carboxylic acid tert-butyl ester

HRID 1993690
ノート
印刷プレビュー

反応式

HRID 1993690 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[C:30]([C:34]1[CH:35]=[C:36]([NH:46][C:47](=O)[O:48]CC(Cl)(Cl)Cl)[N:37]([C:39]2[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][CH:40]=2)[N:38]=1)([CH3:33])([CH3:32])[CH3:31].CCOC(C)=O>CS(C)=O.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:47]([NH:46][C:36]3[N:37]([C:39]4[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][CH:40]=4)[N:38]=[C:34]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:35]=3)=[O:48])=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 99310942,2,2-Trichloroethyl 3-tert-butyl-1-P-tolyl-1H-pyrazol-5-ylcarbamateHCID 17999304tert-Butyl 4-(5-aminopyridin-2-yl)piperazine-1-carboxylate

生成物 1

HCID 685419004-{5-[3-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-ureido]-pyridin-2-yl}-piperazine-1-carboxylic acid tert-butyl ester収率 85.6%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

実験手順

Place 4-(5-amino-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester (200 mg, 0.718 mmol), diisopropylethylamine (0.125 mL, 0.718 mmol), and (5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-carbamic acid, 2,2,2-trichloro-ethyl ester (Preparation 38, 291 mg, 0.718 mmol) in DMSO (5 mL) and heat to 75° C. for 17 hours. Cool to room temperature and add EtOAc and water. Separate organic layer and wash with saturated aq. sodium chloride (2×20 mL). Collect organic layer, dry over Mg2SO4, filter, and concentrate under reduced pressure. Subject residue to silica gel chromatography eluting with 0-70% EtOAc:hexane to yield 328 mg (85%) of 4-{5-[3-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-ureido]-pyridin-2-yl}-piperazine-1-carboxylic acid tert-butyl ester. MS(ES+): m/z=534.4 [M+H]).

後処理

  1. washSeparate organic layer and wash with saturated aq. sodium chloride (2×20 mL)
  2. dry with materialCollect organic layer, dry over Mg2SO4
  3. filtrationfilter
  4. concentrationconcentrate under reduced pressure
  5. washSubject residue to silica gel chromatography eluting with 0-70% EtOAc

出典と根拠

ORDレコード
ord-fa0f13cd7fc44a7bb01f1a45c0616fee
出典データセット
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07652015B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート