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Ethyl Acetate → 1-methyl-5-(2-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-6-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 588422
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HRID 588422 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:16]=[C:10]3[CH:11]=[CH:12][C:13]([NH2:15])=[CH:14][N:9]3[N:8]=2)[CH:2]=1.[CH2:17]([O:19][C:20]([C:22]1[CH:23]=[N:24][N:25]([CH3:30])[C:26]=1[C:27](O)=[O:28])=[O:21])[CH3:18].CCCP(=O)=O.C(OCC)(=O)C.C(N(CC)C(C)C)(C)C>O1CCCC1>[CH2:17]([O:19][C:20]([C:22]1[CH:23]=[N:24][N:25]([CH3:30])[C:26]=1[C:27](=[O:28])[NH:15][C:13]1[CH:12]=[CH:11][C:10]2[N:9]([N:8]=[C:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[N:16]=2)[CH:14]=1)=[O:21])[CH3:18]
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참가 물질

7

반응물 5

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 16167369Propylphosphoric anhydrideHCID 252475674-(Ethoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acidHCID 717437892-(Pyridin-3-YL)-[1,2,4]triazolo[1,5-A]pyridin-6-amine

생성물 1

HCID 89463942
1-methyl-5-(2-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-6-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid ethyl ester
수율 93%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
70 °C

실험 절차

A mixture of 2-(pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-6-ylamine (480 mg, 2.27 mmol), 4-(ethoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acid (495 mg, 2.5 mmol), propylphosphonic anhydride in ethyl acetate 50% (3.62 g, 3.35 ml, 5.68 mmol) and N,N-diisopropylethylamine (1.17 g, 1.55 ml, 9.09 mmol) in tetrahydrofuran (10 ml) was stirred for 18 hours at 70° C. The solvent was evaporated under reduced pressure, the residue was triturated with saturated aqueous sodium hydrogencarbonate. The precipitated solid was filtered off, washed with water and dried in vacuo, affording 1-methyl-5-(2-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-6-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid ethyl ester (825 mg, 93%) as light brown solid. Mp.: 217° C. MS: m/z=392.1 (M+H+).

후처리

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was triturated with saturated aqueous sodium hydrogencarbonate
  3. filtrationThe precipitated solid was filtered off
  4. washwashed with water
  5. customdried in vacuo

출처 및 근거

ORD 기록
ord-f16732f31faf40969a5e6a0867314264
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09227970B2

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