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Azetidine → 4-(azetidine-1-carbonyl)-N-(2-(dimethylamino)-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1-methyl-1H-pyrazole-5-carboxamide

HRID 1802207
ノート
印刷プレビュー

反応式

HRID 1802207 の反応式
[CH3:1][N:2]([CH3:24])[C:3]1[N:23]=[C:6]2[CH:7]=[C:8]([NH:11][C:12]([C:14]3[N:18]([CH3:19])[N:17]=[CH:16][C:15]=3[C:20](O)=[O:21])=[O:13])[CH:9]=[CH:10][N:5]2[N:4]=1.[NH:25]1[CH2:28][CH2:27][CH2:26]1.CCCP(=O)=O.C(N(C(C)C)CC)(C)C>O1CCCC1>[N:25]1([C:20]([C:15]2[CH:16]=[N:17][N:18]([CH3:19])[C:14]=2[C:12]([NH:11][C:8]2[CH:9]=[CH:10][N:5]3[N:4]=[C:3]([N:2]([CH3:1])[CH3:24])[N:23]=[C:6]3[CH:7]=2)=[O:13])=[O:21])[CH2:28][CH2:27][CH2:26]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 10422AzetidineHCID 81531DiisopropylethylamineHCID 16167369Propylphosphoric anhydrideHCID 677751075-(2-(dimethylamino)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylic acid

生成物 1

HCID 573777464-(azetidine-1-carbonyl)-N-(2-(dimethylamino)-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1-methyl-1H-pyrazole-5-carboxamide収率 71%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 5-(2-(dimethylamino)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylic acid (150 mg, 455 μmol), azetidine (123 l, 1.82 mmol), propylphosphonic anhydride (50% in ethyl acetate, 671 μl, 1.14 mmol) and diisopropylethylamine (398 μl, 2.28 mmol) in tetrahydrofurane (8 ml) is stirred for 18 hours at room temperature under nitrogen atmosphere. The solvent is evaporated and the residue triturated with sat. aqueous sodium hydrogencarbonate solution. The precipitated solid is collected by filtration, washed with water and dried affording 4-(azetidine-1-carbonyl)-N-(2-(dimethylamino)-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1-methyl-1H-pyrazole-5-carboxamide (119 mg, 70.9%) as an off-white solid. Mp.: 240-1° C. MS: m/z=369.1 (M+H+).

後処理

  1. customThe solvent is evaporated
  2. customthe residue triturated with sat. aqueous sodium hydrogencarbonate solution
  3. filtrationThe precipitated solid is collected by filtration
  4. washwashed with water
  5. customdried

出典と根拠

ORDレコード
ord-c4cb52ef91f749c5bd58f4e14314e590
出典データセット
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08349824B2

反応ノート

読み込み中…

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