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

HRID 1802249ノート

反応式

HRID 1802249 の反応式
[Br:1][C:2]1[N:11]=[C:5]2[CH:6]=[C:7]([NH2:10])[CH:8]=[CH:9][N:4]2[N:3]=1.[CH2:12]([O:14][C:15]([C:17]1[CH:18]=[N:19][N:20]([CH3:25])[C:21]=1[C:22](O)=[O:23])=[O:16])[CH3:13].CCCP(=O)=O.C(N(CC)C(C)C)(C)C>O1CCCC1>[CH2:12]([O:14][C:15]([C:17]1[CH:18]=[N:19][N:20]([CH3:25])[C:21]=1[C:22](=[O:23])[NH:10][C:7]1[CH:8]=[CH:9][N:4]2[N:3]=[C:2]([Br:1])[N:11]=[C:5]2[CH:6]=1)=[O:16])[CH3:13]

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 16167369Propylphosphoric anhydrideHCID 252475674-(Ethoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acidHCID 677745572-Bromo-[1,2,4]triazolo[1,5-a]pyridin-7-amine

生成物 1

HCID 67775496ethyl 5-(2-bromo-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylate収率 82.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 2-bromo-[1,2,4]triazolo[1,5-a]pyridin-7-amine (2.39 g, 11.2 mmol), 4-(ethoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acid (2.22 g, 11.2 mmol), propylphosphonic anhydride (50% in ethyl acetate, 16.5 ml, 28.0 mmol) and N,N-diisopropylethylamine (5.72 ml, 33.7 mmol) in tetrahydrofuran (80 ml) was refluxed for 18 hours under argon atmosphere. The solvent was evaporated and the resulting yellowish oil was triturated with sat. sodium hydrogencarbonate solution. The precipitated solid was filtered off, washed with water 4 times and dried in vacuo affording 5-(2-bromo-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (3.64 g, 82.5%) as a light yellow solid. mp: 177-180° C., MS: m/z=393.0/395.0 (M+H+)

後処理

  1. temperaturewas refluxed for 18 hours under argon atmosphere
  2. customThe solvent was evaporated
  3. customthe resulting yellowish oil was triturated with sat. sodium hydrogencarbonate solution
  4. filtrationThe precipitated solid was filtered off
  5. washwashed with water 4 times
  6. customdried in vacuo

出典と根拠

ORDレコード
ord-89a362b08e7e4e50b4380b5548f4dee0
出典データセット
uspto-grants-2013_01
特許番号
US08349824B2

反応ノート

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