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Triethylamine → HCID 178434267, 화합물

HRID 490100
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HRID 490100 반응식
[C:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:15]=[C:16](Cl)[N:17]=[N:18][CH:19]=2)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:21][C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([Sn](C)(C)C)[CH:29]=2)[NH:24][N:23]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C>[CH3:21][C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([C:16]3[N:17]=[N:18][CH:19]=[C:14]([N:11]4[CH2:12][CH2:13][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9][CH2:10]4)[N:15]=3)[CH:29]=2)[NH:24][N:23]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 576741865-(4-Boc-piperazin-1-yl)-3-chloro[1,2,4]triazineHCID 178434313HCID 178434313, 화합물

생성물 1

HCID 178434267HCID 178434267, 화합물수율 7.8%

시약·촉매·용매 3

HCID 9811564
Bis(dibenzylideneacetone)palladium
촉매
HCID 6228Dimethylformamide용매
HCID 8857Ethyl Acetate용매

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온도
180 °C

실험 절차

To a solution of 5-(4-Boc-piperazin-1-yl)-3-chloro[1,2,4]triazine 151 (50 mg, 0.167 mmol.) in anhydrous DMF (3 mL) was added 3-methyl-5-trimethylstannanylindazole 152 (49 mg, 0.166 mmol.), tris(dibenzylideneacetone)dipalladium (15 mg, 0.016 mmol.), tri-o-tolylphosphine (10 mg, 0.033 mmol.) and triethylamine (17 mg, 0.168 mmol.). The reaction mixture was heated in a microwave reactor at 180° C. for 20 minutes. Ethyl acetate (50 mL) was added. The organic layer was washed with water and brine. The organic layer was filtered through Celite and dried over sodium sulfate. The organic solvent was evaporated under reduced pressure. The crude product was purified by RP-HPLC to yield the desired 3-(3-methylindazol-5-yl)-5-(4-Boc-piperazin-1-yl)-[1,2,4]triazine 153 (5.1 mg, 0.013 mmol.).

후처리

  1. washThe organic layer was washed with water and brine
  2. filtrationThe organic layer was filtered through Celite
  3. dry with materialdried over sodium sulfate
  4. customThe organic solvent was evaporated under reduced pressure
  5. customThe crude product was purified by RP-HPLC

출처 및 근거

ORD 기록
ord-ec2fe657d51a4462b46fa39df0e076ec
출처 데이터셋
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07528132B2

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