N-Methylethylamine → N4-ethyl-N4,1-dimethyl-N5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1H-pyrazole-4,5-dicarboxamide

HRID 1802143노트

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HRID 1802143 반응식
[CH3:1][N:2]1[C:6]([C:7](=[O:24])[NH:8][C:9]2[CH:14]=[CH:13][N:12]3[N:15]=[C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[N:17]=[C:11]3[CH:10]=2)=[C:5]([C:25]([OH:27])=O)[CH:4]=[N:3]1.[CH2:28]([NH:30][CH3:31])[CH3:29].CCCP(=O)=O>O1CCCC1.C(OCC)(=O)C>[CH2:28]([N:30]([CH3:31])[C:25]([C:5]1[CH:4]=[N:3][N:2]([CH3:1])[C:6]=1[C:7]([NH:8][C:9]1[CH:14]=[CH:13][N:12]2[N:15]=[C:16]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:17]=[C:11]2[CH:10]=1)=[O:24])=[O:27])[CH3:29]

참가 물질

6

반응물 3

HCID 12219N-MethylethylamineHCID 16167369Propylphosphoric anhydrideHCID 573789541-methyl-5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid

생성물 1

HCID 57378956N4-ethyl-N4,1-dimethyl-N5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1H-pyrazole-4,5-dicarboxamide수율 54.6%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
70 °C

실험 절차

A mixture of 1-methyl-5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid (600 mg, 1.66 mmol), N-ethylmethylamine (427 ul, 4.97 mmole), N-diisopropylethylamine (868 ul, 4.97 mmol) and propylphosphonic anhydride (50% in ethyl acetate, 2.44 ml, 4.14 mmol) in tetrahydrofurane (30 ml) is stirred for 2 hours at 70° C. The cooled solution is diluted with ethyl acetate, washed once with sat. aqueous sodium bicarbonate solution, once with brine, dried with magnesium sulfate and evaporated to dryness. Two successive crystallizations of the residue (680 mg white solid) from ethyl acetate afford N4-ethyl-N4,1-dimethyl-N5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1H-pyrazole-4,5-dicarboxamide (365 mg, 54.6%) as a white solid. mp.: 193-4° C. MS: m/z=404.3 (M+H+).

후처리

  1. washwashed once with sat. aqueous sodium bicarbonate solution, once with brine
  2. dry with materialdried with magnesium sulfate
  3. customevaporated to dryness
  4. customTwo successive crystallizations of the residue (680 mg white solid) from ethyl acetate

출처 및 근거

ORD 기록
ord-a5639e7330b74f1ca8e0ff136af6af50
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08349824B2

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