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Diethyl Ether → 4-{5-[3-(5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl)-ureido]-6-methyl-pyridin-2-yl}-piperazine-1-carboxylic acid tert-butyl ester

HRID 1993688
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HRID 1993688 반응식
[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])=[C:16]([CH3:21])[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:22]([C:26]1[CH:27]=[C:28]([NH:38][C:39](=O)[O:40]CC(Cl)(Cl)Cl)[N:29]([C:31]2[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=2)[N:30]=1)([CH3:25])([CH3:24])[CH3:23].CCN(C(C)C)C(C)C.C(OCC)C>CS(C)=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:39]([NH:38][C:28]3[N:29]([C:31]4[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=4)[N:30]=[C:26]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:27]=3)=[O:40])=[C:16]([CH3:21])[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 81531DiisopropylethylamineHCID 99310942,2,2-Trichloroethyl 3-tert-butyl-1-P-tolyl-1H-pyrazol-5-ylcarbamateHCID 591344511-Boc-4-(5-amino-6-methyl-2-pyridinyl)piperazine

생성물 1

HCID 685368704-{5-[3-(5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl)-ureido]-6-methyl-pyridin-2-yl}-piperazine-1-carboxylic acid tert-butyl ester수율 89%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매2회

실험 절차

Heat a solution of 4-(5-amino-6-methyl-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester (Preparation 3, 41.20 g, 140.9 mmol), (5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-carbamic acid, 2,2,2-trichloro-ethyl ester (Preparation 38, 57.03 g, 140.9 mmol), and DIEA (36.8 mL, 211.4 mmol) in DMSO (500 mL) at 60-65° C. for 2.5 hours. Add additional DMSO (100 mL) during the last 30 min to the thick slurry. Cool the slurry to room temperature and allow to stand overnight. Add diethyl ether (600 mL) and stir the slurry for 1 hour at room temperature. Filter and wash with diethyl ether (5×300 mL) then air-dry to afford a white solid (68.70 g, 89% yield uncorrected for DMSO—contains ca. 85 mol % of DMSO. LCMS(ES+): m/z=548 [M+H].

후처리

  1. filtrationFilter
  2. washwash with diethyl ether (5×300 mL)
  3. customthen air-dry
  4. customto afford a white solid (68.70 g, 89% yield uncorrected for DMSO—contains ca. 85 mol % of DMSO. LCMS(ES+)

출처 및 근거

ORD 기록
ord-6f3675c6de2f4513abe105e261972924
출처 데이터셋
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07652015B2

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