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Diisopropylethylamine → 1-methyl-5-(2-pyrrolidin-1-yl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 1802239
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반응식

HRID 1802239 반응식
[N:1]1([C:6]2[N:15]=[C:9]3[CH:10]=[C:11]([NH2:14])[CH:12]=[CH:13][N:8]3[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:16]([O:18][C:19]([C:21]1[CH:22]=[N:23][N:24]([CH3:29])[C:25]=1[C:26](O)=[O:27])=[O:20])[CH3:17].CCCP(=O)=O.C(N(CC)C(C)C)(C)C>O1CCCC1>[CH2:16]([O:18][C:19]([C:21]1[CH:22]=[N:23][N:24]([CH3:29])[C:25]=1[C:26](=[O:27])[NH:14][C:11]1[CH:12]=[CH:13][N:8]2[N:7]=[C:6]([N:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[N:15]=[C:9]2[CH:10]=1)=[O:20])[CH3:17]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 16167369Propylphosphoric anhydrideHCID 252475674-(Ethoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acidHCID 677741812-(Pyrrolidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-amine

생성물 1

HCID 677763851-methyl-5-(2-pyrrolidin-1-yl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid ethyl ester수율 88%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 2-(pyrrolidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-amine (197 mg, 969 μmol), 4-(ethoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acid (231 mg, 1.16 mmol), propylphosphonic anhydride (50% in ethyl acetate, 1.43 ml, 2.42 mmol) and N,N-diisopropylethylamine (494 μl, 2.91 mmol) in tetrahydrofuran (10 ml) was refluxed for 18 hours. The solvent was evaporated, the residue was triturated with sodium hydrogencarbonate solution. The precipitated solid was filtered off, washed with water and dried affording 1-methyl-5-(2-pyrrolidin-1-yl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid ethyl ester (327 mg, 88.0%) as a light brown solid. mp: 233-234° C., MS: m/z=384.5 (M+H+).

후처리

  1. temperaturewas refluxed for 18 hours
  2. customThe solvent was evaporated
  3. customthe residue was triturated with sodium hydrogencarbonate solution
  4. filtrationThe precipitated solid was filtered off
  5. washwashed with water
  6. customdried

출처 및 근거

ORD 기록
ord-7e3111d4b7dd4e74bf8d8c915318b1d3
출처 데이터셋
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08349824B2

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