Thiophene-2-carbohydrazide → HCID 178508342、化合物

HRID 646758ノート

反応式

HRID 646758 の反応式
[NH2:1][C:2]1[C:3]([C:16]#[N:17])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][OH:15])[CH:9]=2)=[CH:6][N:7]=1.[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23]([NH:25][NH2:26])=O.C[O-].[Na+]>CO>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([CH2:14][OH:15])[CH:11]=[CH:12][CH:13]=2)=[N:4][C:3]=1[C:16]1[NH:26][N:25]=[C:23]([C:19]2[S:18][CH:22]=[CH:21][CH:20]=2)[N:17]=1

参加物

5

反応物 3

HCID 73098Thiophene-2-carbohydrazideHCID 10942334Sodium MethoxideHCID 587105723-Amino-6-[3-(hydroxymethyl)phenyl]pyrazine-2-carbonitrile

生成物 1

HCID 178508342HCID 178508342、化合物収率 6.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 3-amino-6-[3-(hydroxymethyl)phenyl]pyrazine-2-carbonitrile (149 mg, 0.74 mmol) was added thiophene-2-carboxylic acid hydrazide (94 mg, 0.66 mmol), sodium methoxide (53 mg, 0.996 mmol) in MeOH (5 mL). After reflux for 4 days, the reaction mixture was extracted with ethyl acetate (10 mL×3) and dried over MgSO4. Filteraction and concentration in vacuo gave a crude product, which was purified by preparative HPLC (0.1% TFA in water/0.1% TFA in CH3CN). The product fractions were neutralized by aqueous saturated sodium bicarbonate solution and partitioned with ethyl acetate. The aqueous phase was extracted once with additional ethyl acetate. The combined organic layers were washed with saturated aqueous sodium chloride then dried over anhydrous magnesium sulfate. Filtration and concentration in vacuo gave the (3-{5-amino-6-[3-(2-thienyl)-1H-1,2,4-triazol-5-yl]pyrazin-2-yl } phenyl)methanol (14 mg, yield): 1H NMR (400 MHz, CD3OD): δ 8.65 (s, 1H), 8.14 (s, 1H), 8.02 (d, 1H), 7.77 (m, 1H), 7.53 (m, 1H), 7.47 (m, 1H), 7.38 (m, 1H), 7.17 (m, 1H), 4.72 (s, 2H); MS (EI) for C17H14N6O: 351.10 (MH+).

後処理

  1. temperatureAfter reflux for 4 days
  2. extractionthe reaction mixture was extracted with ethyl acetate (10 mL×3)
  3. dry with materialdried over MgSO4
  4. concentrationFilteraction and concentration in vacuo
  5. customgave a crude product, which
  6. customwas purified by preparative HPLC (0.1% TFA in water/0.1% TFA in CH3CN)
  7. custompartitioned with ethyl acetate
  8. extractionThe aqueous phase was extracted once with additional ethyl acetate
  9. washThe combined organic layers were washed with saturated aqueous sodium chloride
  10. dry with materialthen dried over anhydrous magnesium sulfate
  11. filtrationFiltration and concentration in vacuo

出典と根拠

ORDレコード
ord-2a00e6cfa46743768aef5eed1863e213
出典データセット
uspto-grants-2010_04
特許番号
US07704995B2

反応ノート

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