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3-Amino-2-pyrazinecarboxylic acid → 3-amino-N-(4-fluoro-2-hydroxyphenyl)pyrazine-2-carboxamide

HRID 908379
ノート
印刷プレビュー

反応式

HRID 908379 の反応式
[NH2:1][C:2]1[N:3]=[CH:4][C:5](C2C=NN(C3CCN(C(OC(C)(C)C)=O)CC3)C=2)=[N:6][C:7]=1[C:8]1[O:9][C:10]2[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:11]=2[N:12]=1.NC1C(C(O)=[O:44])=NC=CN=1.NC1C=CC(F)=CC=1O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C.C(N(CC)CC)C>[NH2:1][C:2]1[C:7]([C:8]([NH:12][C:11]2[CH:13]=[CH:14][C:15]([F:17])=[CH:16][C:10]=2[OH:9])=[O:44])=[N:6][CH:5]=[CH:4][N:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 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)HCID 67387653Tert-butyl 4-[4-[5-amino-6-(6-fluoro-1,3-benzoxazol-2-yl)pyrazin-2-yl]pyrazol-1-yl]piperidine-1-carboxylate

生成物 1

HCID 136374732
3-amino-N-(4-fluoro-2-hydroxyphenyl)pyrazine-2-carboxamide

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

The tert-butyl 4-[4-[5-amino-6-(6-fluoro-1,3-benzoxazol-2-yl)pyrazin-2-yl]pyrazol-1-yl]piperidine-1-carboxylate used as starting material was prepared as follows: 3-aminopyrazine-2-carboxylic acid (5 g) and 2-amino-5-fluoro-phenol (5.94 g) were dissolved in DMF (30 ml). Triethylamine (5.81 g) and HATU (19.13 g) were added to the solution. The resulting mixture was stirred at room temperature for 24 hours, diluted with ethyl acetate (100 ml) and washed with brine (3×20 ml). The organic layer was dried over sodium sulfate. The precipitate was collected, recrystallized in ethanol and further purified by chromatography on silica gel (hexane/ethyl acetate/Methanol) to give 3-amino-N-(4-fluoro-2-hydroxy-phenyl)pyrazine-2-carboxamide (6 g). NMR Spectrum: (400 MHz, DMSOd6) 10.8 (s, 1H), 10.2 (s, 1H), 8.30 (m, 2H), 7.80 (s, 1H), 7.50 (br, 2H), 6.60 (m, 2H). Mass spectrum: M+H+ 249.

後処理

  1. customwas prepared
  2. washwashed with brine (3×20 ml)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customThe precipitate was collected
  5. customrecrystallized in ethanol
  6. customfurther purified by chromatography on silica gel (hexane/ethyl acetate/Methanol)

出典と根拠

ORDレコード
ord-9394b6aa5817401182d05fa1caa06630
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

読み込み中…

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