2-Aminopyridine-4-carbohydrazide → (3-{5-amino-6-[3-(2-aminopyridin-4-yl)-1H-1,2,4-triazol-5-yl]pyrazin-2-yl}phenyl)methanol

HRID 646759Notes

Reaction equation

HRID 646759 reaction equation
[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.[NH2:18][C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][N:28]=1)[C:22]([NH:24][NH2:25])=O>CN(C=O)C>[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:25][N:24]=[C:22]([C:21]2[CH:26]=[CH:27][N:28]=[C:19]([NH2:18])[CH:20]=2)[N:17]=1

Participants

4

Reactant 2

HCID 3225522-Aminopyridine-4-carbohydrazideHCID 587105723-Amino-6-[3-(hydroxymethyl)phenyl]pyrazine-2-carbonitrile

Product 1

HCID 68650742(3-{5-amino-6-[3-(2-aminopyridin-4-yl)-1H-1,2,4-triazol-5-yl]pyrazin-2-yl}phenyl)methanolYield 5.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
180 °C

Procedure

To a solution of of 3-amino-6-[3-(hydroxymethyl)phenyl]pyrazine-2-carbonitrile (250 mg, 1.11 mmol) was added 2-aminoisonicotinic acid hydrazide (311 mg, 2.04 mmol). After being heated at 180° C. for 90 min, the reaction mixture was dissolved in DMF and washed with water, ethyl acetate (10 mL×3). 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 a crude oil, which was purified by preparative HPLC to yield (3-{5-amino-6-[3-(2-aminopyridin-4-yl)-1H-1,2,4-triazol-5-yl]pyrazin-2-yl}phenyl)methanol (23.2 mg, 5.7% yield): 1H NMR (400 MHz, DMSO-d6): δ 8.80 (s, 1H), 8.15 (s, 1H), 8.10 (m, 1H), 7.70 (m, 2H), 7.43 (m, 2H), 7.20 (m, 1H), 6.10 (s, 2H), 5.25 (m, 1H) 4.60 (m, 1H); MS (EI) for C18H16N8O: 361.11 (MH+).

Workup

  1. washwashed with water, ethyl acetate (10 mL×3)
  2. extractionThe aqueous phase was extracted once with additional ethyl acetate
  3. washThe combined organic layers were washed with saturated aqueous sodium chloride
  4. dry with materialthen dried over anhydrous magnesium sulfate
  5. filtrationFiltration and concentration in vacuo
  6. customgave a crude oil, which
  7. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-0c65b7c9be9b476cabcae692e896ca8c
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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