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Dimethylformamide → 3-amino-N-(4-fluoro-2-hydroxyphenyl)pyrazine-2-carboxamide

HRID 908458
ノート
印刷プレビュー

反応式

HRID 908458 の反応式
[NH2:1][C:2]1[C:3]([C:8]([OH:10])=O)=[N:4][CH:5]=[CH:6][N:7]=1.[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[OH:19].CN(C=O)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(OCC)(=O)C.C(N(CC)CC)C>[NH2:1][C:2]1[C:3]([C:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[OH:19])=[O:10])=[N:4][CH:5]=[CH:6][N:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 726563-Amino-2-pyrazinecarboxylic acidHCID 1857632-Amino-5-fluorophenolHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

生成物 1

HCID 1363747323-amino-N-(4-fluoro-2-hydroxyphenyl)pyrazine-2-carboxamide収率 67.3%

試薬・触媒・溶媒

2
HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

3-Aminopyrazine-2-carboxylic acid (5 g) and 2-amino-5-fluorophenol (5.9 g) were dissolved into DMF (30 ml). Triethylamine (5.8 g) and HATU (19.2 g) were added to the mixture. The resulting mixture was stirred at room temperature for 24 hours. Ethyl acetate (100 ml) was added to the mixture. The resulting mixture was washed with brine (20 ml×3). The organic phase was dried and concentrated. The resulting residue was purified by chromatography on silica gel to give 3-amino-N-(4-fluoro-2-hydroxyphenyl)pyrazine-2-carboxamide (6 g). NMR Spectrum: (DMSOd6, 400 MHz) 6.60 (m, 2H), 7.50 (br s, 2H), 7.80 (s, 1H), 8.30 (m, 2H), 10.2 (s, 1H), 10.8 (s, 1H); Mass spectrum: MH+ 249.

後処理

  1. washThe resulting mixture was washed with brine (20 ml×3)
  2. customThe organic phase was dried
  3. concentrationconcentrated
  4. customThe resulting residue was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-fab963135df648e081a934a37eea9263
出典データセット
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08017611B2

反応ノート

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