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Triethylamine → 2-Phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid [6-(acetyl-methyl-amino)-pyridin-3-yl]-amide

HRID 2236222
ノート
印刷プレビュー

反応式

HRID 2236222 の反応式
[C:1]1([C:7]2[O:8][C:9]([C:15]([F:18])([F:17])[F:16])=[C:10]([C:12]([OH:14])=O)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:19][C:20]1[CH:21]=[CH:22][C:23]([N:26]([CH3:30])[C:27](=[O:29])[CH3:28])=[N:24][CH:25]=1.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.C(N(CC)CC)C>ClCCl>[C:27]([N:26]([CH3:30])[C:23]1[N:24]=[CH:25][C:20]([NH:19][C:12]([C:10]2[N:11]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[O:8][C:9]=2[C:15]([F:18])([F:17])[F:16])=[O:14])=[CH:21][CH:22]=1)(=[O:29])[CH3:28]
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 8471TriethylamineHCID 2733179PyBroPHCID 27764382-Phenyl-5-(trifluoromethyl)-oxazole-4-carboxylic acidHCID 59301435N-(5-aminopyridin-2-yl)-N-methylacetamide

生成物 1

HCID 593013352-Phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid [6-(acetyl-methyl-amino)-pyridin-3-yl]-amide

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

A mixture of 2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (260 mg, 1 mmol), N-(5-amino-pyridin-2-yl)-N-methyl-acetamide (165 mg, 1 mmol), bromo-tri-pyrrolidino-phosphonium hexafluorophosphate (470 mg, 1 mmol), and triethylamine (202 mg, 2 mmol) in anhydrous dichloromethane (5 mL) was stirred at room temperature overnight. After the reaction was complete, the solvent and excess triethylamine were removed by evaporation. Flash chromatography (Merck silica gel 60, 230-400 mesh, 0%-40% ethyl acetate in hexane for 20 min) gave 2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid [6-(acetyl-methyl-amino)-pyridin-3-yl]-amide as a yellow solid. LCMS calcd for C19H15F3N4O3 (m/e) 404, obsd 405 (M+H).

後処理

  1. customthe solvent and excess triethylamine were removed by evaporation

出典と根拠

ORDレコード
ord-2ebdb6c29b2b41a18ae028e4f8b32459
出典データセット
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07714126B2

反応ノート

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