Thiophene-2-carbohydrazide → HCID 178508342, 화합물

HRID 646758노트

반응식

HRID 646758 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 178508342HCID 178508342, 화합물수율 6.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-2a00e6cfa46743768aef5eed1863e213
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07704995B2

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