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Pyrrolidine → N-(2-(dimethylamino)-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1-methyl-4-(pyrrolidine-1-carbonyl)-1H-pyrazole-5-carboxamide

HRID 1802209
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HRID 1802209 반응식
[CH3:1][N:2]([CH3:24])[C:3]1[N:23]=[C:6]2[CH:7]=[C:8]([NH:11][C:12]([C:14]3[N:18]([CH3:19])[N:17]=[CH:16][C:15]=3[C:20](O)=[O:21])=[O:13])[CH:9]=[CH:10][N:5]2[N:4]=1.[NH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1.CCCP(=O)=O.C(N(C(C)C)CC)(C)C>O1CCCC1>[CH3:1][N:2]([CH3:24])[C:3]1[N:23]=[C:6]2[CH:7]=[C:8]([NH:11][C:12]([C:14]3[N:18]([CH3:19])[N:17]=[CH:16][C:15]=3[C:20]([N:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)=[O:21])=[O:13])[CH:9]=[CH:10][N:5]2[N:4]=1
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6

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HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 16167369Propylphosphoric anhydrideHCID 677751075-(2-(dimethylamino)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylic acid

생성물 1

HCID 57377849N-(2-(dimethylamino)-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1-methyl-4-(pyrrolidine-1-carbonyl)-1H-pyrazole-5-carboxamide수율 89.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
70 °C

실험 절차

A mixture of 5-(2-(dimethylamino)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylic acid (150 mg, 455 μmol), pyrrolidine (226 μl, 2.73 mmol), propylphosphonic anhydride (50% in ethyl acetate, 671 μl, 1.14 mmol) and diisopropylethylamine (239 μl, 1.37 mmol) in tetrahydrofurane (8 ml) is stirred for 18 hours at 70° C. under nitrogen atmosphere. The solvent is evaporated and the residue triturated with sat. aqueous sodium hydrogencarbonate solution. The precipitated solid is collected by filtration, washed with water and dried affording N-(2-(dimethylamino)-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1-methyl-4-(pyrrolidine-1-carbonyl)-1H-pyrazole-5-carboxamide (155 mg, 89%) as a light brown solid. Mp.: 199-201° C. MS: m/z=383.4 (M+H+).

후처리

  1. customThe solvent is evaporated
  2. customthe residue triturated with sat. aqueous sodium hydrogencarbonate solution
  3. filtrationThe precipitated solid is collected by filtration
  4. washwashed with water
  5. customdried

출처 및 근거

ORD 기록
ord-ae48e6e0e2e043fcb15e46c7fe90addc
출처 데이터셋
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08349824B2

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