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 1802187노트

반응식

HRID 1802187 반응식
[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

참가 물질

6

반응물 4

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

생성물 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)-amide수율 43.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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+).

후처리

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

출처 및 근거

ORD 기록
ord-ba28fd6c46754f0494c5c8f23b8acb9a
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08349824B2

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