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Diisopropylethylamine → 6-(3-ethoxyphenyl)-N-[[2-(trifluoromethyl)-1H-indol-5-yl]methyl]pyridine-3-carboxamide

HRID 388390
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HRID 388390 반응식
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:25]([O:27][C:28]1[CH:29]=[C:30]([C:34]2[N:39]=[CH:38][C:37]([C:40]([OH:42])=O)=[CH:36][CH:35]=2)[CH:31]=[CH:32][CH:33]=1)[CH3:26].CCN(C(C)C)C(C)C.[F:52][C:53]([F:66])([F:65])[C:54]1[NH:55][C:56]2[C:61]([CH:62]=1)=[CH:60][C:59]([CH2:63][NH2:64])=[CH:58][CH:57]=2>CN(C=O)C>[CH2:25]([O:27][C:28]1[CH:29]=[C:30]([C:34]2[N:39]=[CH:38][C:37]([C:40]([NH:64][CH2:63][C:59]3[CH:60]=[C:61]4[C:56](=[CH:57][CH:58]=3)[NH:55][C:54]([C:53]([F:66])([F:52])[F:65])=[CH:62]4)=[O:42])=[CH:36][CH:35]=2)[CH:31]=[CH:32][CH:33]=1)[CH3:26]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 532232596-(3-Ethoxyphenyl)nicotinic acid2회HCID 58126817(2-(Trifluoromethyl)-1h-indol-5-yl)methanamine2회

생성물 1

HCID 44466200
6-(3-ethoxyphenyl)-N-[[2-(trifluoromethyl)-1H-indol-5-yl]methyl]pyridine-3-carboxamide
수율 64%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

실험 절차

To a stirred solution of HATU (72.8 mg, 0.192 mmol) in DMF (1 ml) was added 6-[3-(ethyloxy)phenyl]-3-pyridinecarboxylic acid (Intermediate 6, 29 mg, 0.119 mmol) in DMF (0.5 ml), followed by DIPEA (0.050 ml, 0.287 mmol) and finally {[2-(trifluoromethyl)-1H-indol-5-yl]methyl}amine (Intermediate 4, 24 mg, 0.096 mmol) in DMF (1 ml). The solution was stirred for 24 hrs. DMF was removed using a rotary evaporator followed by addition of DCM and sodium bicarbonate solution. The mixture was poured through a phase separation cartridge. The organic layer was evaporated to dryness and purified using MDAP to give the title compound as a white solid (27 mg);

후처리

  1. customDMF was removed
  2. customa rotary evaporator
  3. additionfollowed by addition of DCM and sodium bicarbonate solution
  4. additionThe mixture was poured through a phase separation cartridge
  5. customThe organic layer was evaporated to dryness
  6. custompurified

출처 및 근거

ORD 기록
ord-8dc535b2133b48febdbda5c5486e5255
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08377941B2

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