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Diisopropylethylamine → 1-{5-tert-Butyl-2-[3-(2-hydroxy-ethoxy)-phenyl]-2H-pyrazol-3-yl}-3-{4-[3-((S)-2-methyl-piperidin-1-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy]-cyclohexyl}-urea

HRID 2200047
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HRID 2200047 반응식
ClC(Cl)(Cl)CO[C:5](=[O:26])[NH:6][C:7]1[N:8]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][CH2:24][OH:25])[CH:17]=2)[N:9]=[C:10]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:11]=1.[CH3:29][C@H:30]1[CH2:35][CH2:34][CH2:33][C@@H:32](C)[N:31]1[C:37]1[N:41]2[CH:42]=[C:43]([O:46][CH:47]3[CH2:52][CH2:51][CH:50]([NH2:53])[CH2:49][CH2:48]3)[CH:44]=[CH:45][C:40]2=[N:39][N:38]=1.CCN(C(C)C)C(C)C>O1CCOCC1>[C:12]([C:10]1[CH:11]=[C:7]([NH:6][C:5]([NH:53][CH:50]2[CH2:51][CH2:52][CH:47]([O:46][C:43]3[CH:44]=[CH:45][C:40]4[N:41]([C:37]([N:31]5[CH2:32][CH2:33][CH2:34][CH2:35][C@@H:30]5[CH3:29])=[N:38][N:39]=4)[CH:42]=3)[CH2:48][CH2:49]2)=[O:26])[N:8]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][CH2:24][OH:25])[CH:17]=2)[N:9]=1)([CH3:14])([CH3:13])[CH3:15]
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참가 물질

5

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HCID 81531DiisopropylethylamineHCID 59151941{5-tert-Butyl-2-[3-(2-hydroxy-ethoxy)-phenyl]-2H-pyrazol-3-yl}-carbamic acid 2,2,2-trichloro-ethyl esterHCID 1177290354-[3-((2S,6R)-2,6-Dimethyl-piperidin-1-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy]-cyclohexylamine

생성물 1

HCID 1177291641-{5-tert-Butyl-2-[3-(2-hydroxy-ethoxy)-phenyl]-2H-pyrazol-3-yl}-3-{4-[3-((S)-2-methyl-piperidin-1-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy]-cyclohexyl}-urea
수율 82%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
60 °C

실험 절차

A mixture of {5-tert-butyl-2-[3-(2-hydroxy-ethoxy)-phenyl]-2H-pyrazol-3-yl}-carbamic acid 2,2,2-trichloro-ethyl ester (WO 2007/063868, which is incorporated herein by reference in its entirety, 287.6 mg, 0.638 mmol), Intermediate 18a (140 mg, 0.425 mmol) and DIPEA (223 μL, 1.28 mmol) in dioxane (10 mL) was stirred at 60° C. for 18 h. The volatiles were concentrated in vacuo and the resultant residue was purified by FCC, using 0-10% [2M NH3 in MeOH] in DCM, to afford the title compound (222 mg, 82%). LCMS (Method 3): Rt 3.35 min, m/z 631 [MH+].

후처리

  1. concentrationThe volatiles were concentrated in vacuo
  2. customthe resultant residue was purified by FCC

출처 및 근거

ORD 기록
ord-a9f94e6e741c4c4091970e853863f2a8
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09359354B2

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