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Triethylamine → 1-(3-tert-Butyl-1-(4-cyanophenyl)-1H-pyrazol-5-yl)-3-((5-fluoro-2-(1-(2-hydroxyethyl)-1H-indazole-5-yloxy)phenyl)methyl)urea

HRID 220224
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HRID 220224 반응식
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11](=[O:18])OCC(Cl)(Cl)Cl)[N:7]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:26][CH2:27][C:28]1[CH:46]=[C:45]([F:47])[CH:44]=[CH:43][C:29]=1[O:30][C:31]1[CH:32]=[C:33]2[C:37](=[CH:38][CH:39]=1)[N:36]([CH2:40][CH2:41][OH:42])[N:35]=[CH:34]2.C([N:50](CC)CC)C>CC(N(C)C)=O>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:26][CH2:27][C:28]2[CH:46]=[C:45]([F:47])[CH:44]=[CH:43][C:29]=2[O:30][C:31]2[CH:32]=[C:33]3[C:37](=[CH:38][CH:39]=2)[N:36]([CH2:40][CH2:41][OH:42])[N:35]=[CH:34]3)=[O:18])[N:7]([C:19]2[CH:20]=[CH:21][C:22]([C:25]#[N:50])=[CH:23][CH:24]=2)[N:6]=1)([CH3:2])([CH3:3])[CH3:4]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 99310942,2,2-Trichloroethyl 3-tert-butyl-1-P-tolyl-1H-pyrazol-5-ylcarbamateHCID 445421222-(5-(2-(Aminomethyl)-4-fluorophenoxy)-1H-indazol-1-yl)ethanol

생성물 1

HCID 687836801-(3-tert-Butyl-1-(4-cyanophenyl)-1H-pyrazol-5-yl)-3-((5-fluoro-2-(1-(2-hydroxyethyl)-1H-indazole-5-yloxy)phenyl)methyl)urea수율 32.6%

시약·촉매·용매 1

HCID 31374
Dimethylacetamide
용매

실험 절차

2,2,2-Trichloroethyl 3-tert-butyl-1-p-tolyl-1H-pyrazol-5-ylcarbamate (0.22 g, 0.529 mmol), 2-(5-(2-(aminomethyl)-4-fluorophenoxy)-1H-indazol-1-yl)ethanol (prepared as in Example 1, Steps E1-E6; 0.175 g, 0.582 mmol), and triethylamine were combined in a minimal amount of DMA and stirred at ambient temperature overnight. The reaction mixture was concentrated, and the residue was diluted with DCM. The DCM was washed with aqueous NH4Cl and aqueous Na2CO3. The organic layer was dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography, eluting with 1% MeOH in ethyl acetate to provide 100 mg (32.6%) of the desired product. MS M+1 (568).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. additionthe residue was diluted with DCM
  3. washThe DCM was washed with aqueous NH4Cl and aqueous Na2CO3
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with 1% MeOH in ethyl acetate

출처 및 근거

ORD 기록
ord-8b01769cc7eb4309a298211f140dc960
출처 데이터셋
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08202899B2

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