Diisopropylethylamine → 4-(azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carboxylic acid [2-(3-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-amide

HRID 1802265노트

반응식

HRID 1802265 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[N:29]=[C:12]3[CH:13]=[C:14]([NH:17][C:18]([C:20]4[N:24]([CH3:25])[N:23]=[CH:22][C:21]=4[C:26]([OH:28])=O)=[O:19])[CH:15]=[CH:16][N:11]3[N:10]=2)[CH:6]=[CH:7][CH:8]=1.CN(C(ON1N=NC2C=[CH:42][CH:43]=[N:44][C:39]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.N1CCC1.CCN(C(C)C)C(C)C>CN(C=O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[N:29]=[C:12]3[CH:13]=[C:14]([NH:17][C:18]([C:20]4[N:24]([CH3:25])[N:23]=[CH:22][C:21]=4[C:26]([N:44]4[CH2:43][CH2:42][CH2:39]4)=[O:28])=[O:19])[CH:15]=[CH:16][N:11]3[N:10]=2)[CH:6]=[CH:7][CH:8]=1

참가 물질

7

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 12308726Azetidine hydrochlorideHCID 677739945-[2-(3-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl]-1-methyl-1H-pyrazole-4-carboxylic acid

생성물 1

HCID 573784944-(azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carboxylic acid [2-(3-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-amide수율 44%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
25 °C

실험 절차

To a solution of 5-[2-(3-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl]-1-methyl-1H-pyrazole-4-carboxylic acid (4.0 g, 10.2 mmol) in DMF (50 ml) were added HATU (8.5 g, 22 mmol), azetidine hydrochloride (1.05 g, 93.5 mmol) and DIPEA (7.5 ml, 40 mmol) at 0° C. The resultant reaction mixture was stirred at 25° C. for 16 h. The mixture was diluted with water (100 ml) and stirred for 15 min. The resultant precipitated solid was filtered, washed thoroughly with water, and dried azeotropically with toluene followed by vacuum to yield 4-(azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carboxylic acid [2-(3-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-amide as off-white solid (1.9 g, 44%). LC-MS: m/z=432.4 [M+H]+.

후처리

  1. customThe resultant reaction mixture
  2. stirringstirred for 15 min
  3. customThe resultant precipitated solid
  4. filtrationwas filtered
  5. washwashed thoroughly with water
  6. dry with materialdried azeotropically with toluene

출처 및 근거

ORD 기록
ord-baa2855b4b8b404bb208a3c1baaa85fd
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08349824B2

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