Diisopropylethylamine → 4-(azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carboxylic acid (6-fluoro-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-amide

HRID 1802187ノート

反応式

HRID 1802187 の反応式
[F:1][C:2]1[C:3]([NH2:17])=[CH:4][C:5]2[N:6]([N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.[N:18]1([C:22]([C:24]2[CH:25]=[N:26][N:27]([CH3:32])[C:28]=2[C:29](O)=[O:30])=[O:23])[CH2:21][CH2:20][CH2:19]1.CCCP(=O)=O.C(N(C(C)C)CC)(C)C>O1CCCC1>[F:1][C:2]1[C:3]([NH:17][C:29]([C:28]2[N:27]([CH3:32])[N:26]=[CH:25][C:24]=2[C:22]([N:18]2[CH2:21][CH2:20][CH2:19]2)=[O:23])=[O:30])=[CH:4][C:5]2[N:6]([N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 16167369Propylphosphoric anhydrideHCID 58446922HCID 58446922、化合物HCID 677751876-Fluoro-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-amine

生成物 1

HCID 573777414-(azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carboxylic acid (6-fluoro-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-amide収率 43.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 6-fluoro-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-amine (50 mg, 219 μmol), 4-(azetidine-1-carbonyl)-1-methyl-1H-pyrazole-5-carboxylic acid (45.8 mg, 219 μmol), propylphosphonic anhydride (50% in ethyl acetate, 323 μl, 548 μmol) and diisopropylethyl amine (115 μl, 657 μmol) in tetrahydrofuran (5 ml) was refluxed for 18 hours. The crude material is loaded on silica and purified by flash chromatography on a 20 g silica column using heptane/ethyl acetate 20-100% as eluent, affording 4-(azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carboxylic acid (6-fluoro-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-amide (40 mg: 43.5%) as white solid. Mp.: >250° C. MS: m/z=420.3 (M+H+).

後処理

  1. temperaturewas refluxed for 18 hours
  2. custompurified by flash chromatography on a 20 g silica column

出典と根拠

ORDレコード
ord-ba28fd6c46754f0494c5c8f23b8acb9a
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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