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Diisopropylethylamine → HCID 68540874、化合物

HRID 1993698
ノート
印刷プレビュー

反応式

HRID 1993698 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[C:19]([NH2:21])[CH:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC(Cl)(Cl)C[O:25][C:26](=O)[NH:27][C:28]1[N:29]([C:37]2[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=2)[N:30]=[C:31]([C:33]([CH3:36])([CH3:35])[CH3:34])[CH:32]=1.C(N(C(C)C)CC)(C)C>CS(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[C:19]([NH:21][C:26]([NH:27][C:28]3[N:29]([C:37]4[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=4)[N:30]=[C:31]([C:33]([CH3:36])([CH3:35])[CH3:34])[CH:32]=3)=[O:25])[CH:18]=[CH:17][N:16]=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

5

反応物 3

HCID 81531DiisopropylethylamineHCID 99310942,2,2-Trichloroethyl 3-tert-butyl-1-P-tolyl-1H-pyrazol-5-ylcarbamateHCID 68538138HCID 68538138、化合物

生成物 1

HCID 68540874HCID 68540874、化合物収率 46.9%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

Heat a solution of 4-(4-amino-pyridin-2-yloxy)-piperidine-1-carboxylic acid tert-butyl ester (Preparation 20, 1 g, 3.41 mmol), (5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-carbamic acid 2,2,2-trichloro-ethyl ester (Preparation 38, 1.38 g, 3.41 mmol), and diisopropylethylamine (1.2 mL, 6.82 mmol) in DMSO (15 mL) at 60° C. for 5 d. Cool the resulting mixture to room temperature and partition between water and ethyl acetate using saturated aq. sodium chloride solution to aid phase separation. Extract the aqueous layer with ethyl acetate, wash the combined organic layers twice with water, dry over sodium sulfate and concentrate under reduced pressure. Subject residue to silica gel chromatography eluting with a gradient of ethyl acetate in dichloromethane to give 877 mg (43% yield) of 4-{4-[3-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-ureido]-pyridin-2-yloxy}-piperidine-1-carboxylic acid tert-butyl ester. LCMS ES+(m/z) 549 [M+H].

後処理

  1. custompartition between water and ethyl acetate using saturated aq. sodium chloride solution
  2. customphase separation
  3. extractionExtract the aqueous layer with ethyl acetate
  4. washwash the combined organic layers twice with water
  5. dry with materialdry over sodium sulfate
  6. concentrationconcentrate under reduced pressure
  7. washSubject residue to silica gel chromatography eluting with a gradient of ethyl acetate in dichloromethane

出典と根拠

ORDレコード
ord-99f5589bfa104df185e38a02a189de3f
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