Diisopropylethylamine → 7-{[4-(azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carbonyl]-amino}-[1,2,4]triazolo[1,5-a]pyridine-2-carboxylic acid ethyl ester

HRID 1802193노트

반응식

HRID 1802193 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:10]=[C:4]2[CH:3]=1.[N:16]1([C:20]([C:22]2[CH:23]=[N:24][N:25]([CH3:30])[C:26]=2[C:27](O)=[O:28])=[O:21])[CH2:19][CH2:18][CH2:17]1.CCCP(=O)=O.C(N(C(C)C)CC)(C)C>O1CCCC1>[CH2:14]([O:13][C:11]([C:9]1[N:10]=[C:4]2[CH:3]=[C:2]([NH:1][C:27]([C:26]3[N:25]([CH3:30])[N:24]=[CH:23][C:22]=3[C:20]([N:16]3[CH2:19][CH2:18][CH2:17]3)=[O:21])=[O:28])[CH:7]=[CH:6][N:5]2[N:8]=1)=[O:12])[CH3:15]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 16167369Propylphosphoric anhydrideHCID 58446922HCID 58446922, 화합물HCID 67776028Ethyl 7-amino-[1,2,4]triazolo[1,5-a]pyridine-2-carboxylate

생성물 1

HCID 677752457-{[4-(azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carbonyl]-amino}-[1,2,4]triazolo[1,5-a]pyridine-2-carboxylic acid ethyl ester수율 63.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of ethyl 7-amino-[1,2,4]triazolo[1,5-a]pyridine-2-carboxylate (540 mg, 2.62 mmol), 4-(azetidine-1-carbonyl)-1-methyl-1H-pyrazole-5-carboxylic acid (548 mg, 2.62 mmol), propylphosphonic anhydride (50% in ethyl acetate, 3.86 ml, 6.55 mmol) and diisopropylethylamine (1.37 ml, 7.86 mmol) in tetrahydrofurane (10 ml) is refluxed for 18 hours. The solvent is evaporated and the residue triturated with sat. aqueous sodium hydrogencarbonate solution. The precipitated solid is collected by filtration, washed several times with water and dried affording 7-{[4-(azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carbonyl]-amino}-[1,2,4]triazolo[1,5-a]pyridine-2-carboxylic acid ethyl ester (665 mg, 63.9%) as a light brown solid. mp.: 252-5° C. MS: m/z=398.2 (M+H+).

후처리

  1. temperatureis refluxed for 18 hours
  2. customThe solvent is evaporated
  3. customthe residue triturated with sat. aqueous sodium hydrogencarbonate solution
  4. filtrationThe precipitated solid is collected by filtration
  5. washwashed several times with water
  6. customdried

출처 및 근거

ORD 기록
ord-75502040c1d3433d8c7c67fb2ddc3f38
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08349824B2

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