Diisopropylethylamine → ethyl 5-(2-(dimethylamino)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylate

HRID 1802205노트

반응식

HRID 1802205 반응식
[CH3:1][N:2]([CH3:13])[C:3]1[N:12]=[C:6]2[CH:7]=[C:8]([NH2:11])[CH:9]=[CH:10][N:5]2[N:4]=1.[CH2:14]([O:16][C:17]([C:19]1[CH:20]=[N:21][N:22]([CH3:27])[C:23]=1[C:24](O)=[O:25])=[O:18])[CH3:15].CCCP(=O)=O.C(N(C(C)C)CC)(C)C>O1CCCC1>[CH3:1][N:2]([CH3:13])[C:3]1[N:12]=[C:6]2[CH:7]=[C:8]([NH:11][C:24]([C:23]3[N:22]([CH3:27])[N:21]=[CH:20][C:19]=3[C:17]([O:16][CH2:14][CH3:15])=[O:18])=[O:25])[CH:9]=[CH:10][N:5]2[N:4]=1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 16167369Propylphosphoric anhydrideHCID 252475674-(Ethoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acidHCID 67774846N2,N2-dimethyl-[1,2,4]triazolo[1,5-a]pyridine-2,7-diamine

생성물 1

HCID 67774271ethyl 5-(2-(dimethylamino)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylate수율 89.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of N2,N2-dimethyl-[1,2,4]triazolo[1,5-a]pyridine-2,7-diamine (700 mg, 3.95 mmol), 4-(ethoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acid (812 mg, 4.1 mmol), propylphosphonic anhydride (50% in ethyl acetate, 5.82 ml, 9.88 mmol) and diisopropylethylamine (2.07 ml, 11.9 mmol) in tetrahydrofurane (40 ml) is refluxed for 18 hours under nitrogen atmosphere. The solvent is evaporated and the residue triturated with sat. aqueous sodium hydrogencarbonate solution. The solid is collected by filtration, washed with water and dried affording ethyl 5-(2-(dimethylamino)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylate (1.26 g, 89.3%) as a light brown solid. Mp.: 193-5° C. MS: m/z=358.4 (M+H+).

후처리

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

출처 및 근거

ORD 기록
ord-60bb7fab0f7f4748ab48af2a2db9743e
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08349824B2

반응 노트

불러오는 중…