Pyridine → N-[5-(cyclopropylamino)-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-4-[(dimethylamino)methyl]benzamide

HRID 2382905

반응식

HRID 2382905 반응식
[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[C:12]([NH2:14])[N:13]=[C:9]3[CH:8]=[C:7]([C:15]([F:18])([F:17])[F:16])[CH:6]=2)[CH2:3][CH2:2]1.N1C=CC=CC=1.[CH3:25][N:26]([CH2:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1)[CH3:27]>ClCCl>[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[C:12]([NH:14][C:33](=[O:34])[C:32]4[CH:36]=[CH:37][C:29]([CH2:28][N:26]([CH3:25])[CH3:27])=[CH:30][CH:31]=4)[N:13]=[C:9]3[CH:8]=[C:7]([C:15]([F:16])([F:17])[F:18])[CH:6]=2)[CH2:2][CH2:3]1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 137489654-(N,N-dimethylaminomethyl) benzoyl chlorideHCID 59437445N5-cyclopropyl-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridine-2,5-diamine

생성물 1

HCID 59437472N-[5-(cyclopropylamino)-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-4-[(dimethylamino)methyl]benzamide수율 52%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a reaction vessel containing N5-cyclopropyl-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridine-2,5-diamine ((A18), 77 mg, 0.3 mmol, 1 eq.) and pyridine (0.063 mL, 1.2 mmol, 4 eq.) in dichloromethane (1 mL) was added 4-dimethylaminomethyl-benzoyl chloride (118 mg, 0.6 mmol, 2 eq.) as a solution in dichloromethane (2 mL), dropwise. The vessel was capped and heated to reflux for approximately 16 hours. The reaction mixture was cooled and the solvent removed in vacuo. The residue dissolved in DMSO (1.5 mL) and purified by reverse phase preparatory HPLC to give the title compound as a white solid (65.1 mg, 52%). HPLC, Rt: 2.59 min (purity: 100%). LC/MS M+(ESI): 419.2, M−(ESI) 417.2.

후처리

  1. customThe vessel was capped
  2. temperatureheated
  3. temperatureto reflux for approximately 16 hours
  4. temperatureThe reaction mixture was cooled
  5. customthe solvent removed in vacuo
  6. dissolutionThe residue dissolved in DMSO (1.5 mL)
  7. custompurified by reverse phase preparatory HPLC

출처 및 근거

ORD 기록
ord-21e668023a2d44a6ae77f996b98c7ab0
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263595B2

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