Diisopropylethylamine → 5-bromo-N,N-bis(4-methoxybenzyl)pyrazolo[1,5-a]pyridine-3-carboxamide

HRID 513020노트

반응식

HRID 513020 반응식
[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([C:11]([OH:13])=O)=[C:4]2[CH:3]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:47][O:48][C:49]1[CH:65]=[CH:64][C:52]([CH2:53][NH:54][CH2:55][C:56]2[CH:61]=[CH:60][C:59]([O:62][CH3:63])=[CH:58][CH:57]=2)=[CH:51][CH:50]=1>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([C:11]([N:54]([CH2:53][C:52]3[CH:51]=[CH:50][C:49]([O:48][CH3:47])=[CH:65][CH:64]=3)[CH2:55][C:56]3[CH:57]=[CH:58][C:59]([O:62][CH3:63])=[CH:60][CH:61]=3)=[O:13])=[C:4]2[CH:3]=1

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 714952Bis(4-methoxybenzyl)amineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 685073035-Bromopyrazolo[1,5-a]pyridine-3-carboxylic acid

생성물 1

HCID 682824605-bromo-N,N-bis(4-methoxybenzyl)pyrazolo[1,5-a]pyridine-3-carboxamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 5-bromopyrazolo[1,5-a]pyridine-3-carboxylic acid (I-25) (66 mg, 0.27 mmol) in DMF (3 mL) was added DIEA (0.14 mL) and HATU (0.10 g, 0.27 mmol). The reaction was stirred for 30 minutes at room temperature then bis(4-methoxybenzyl)amine (70 mg, 0.27 mmol) was added. Stirring was continued at room temperature for 12 hours. The reaction was diluted with EtOAc, washed with brine, dried over magnesium sulfate, filtered and reduced to dryness. The crude product was purified by flash column chromatography on silica with hexanes/EtOAc gradient as eluant to yield 5-bromo-N,N-bis(4-methoxybenzyl)pyrazolo[1,5-a]pyridine-3-carboxamide (I-26). 1H NMR (400 MHz, CDCl3) δ 8.50 (d, J=2.4 Hz, 1 H), 8.26 (dd, J=0.4, 7.2 Hz, 1 H), 7.88 (s, 1 H), 7.22 (d, J=8.0 Hz, 4 H), 7.00 (dd, J=2.0, 7.2 Hz, 1 H), 6.91 (d, J=8.4 Hz, 4 H), 4.67 (s, 4 H), 3.82 (s, 6 H). MS m/z 480.1, 482.1 (M+1)+.

후처리

  1. stirringStirring
  2. waitwas continued at room temperature for 12 hours
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customThe crude product was purified by flash column chromatography on silica with hexanes/EtOAc gradient as eluant

출처 및 근거

ORD 기록
ord-f1b7d6d23d1844ac92159804db9ae8f8
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102671B2

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