2-Amino-5-methylpyridine → HCID 59559959, compound

HRID 1177352Notes

Reaction equation

HRID 1177352 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:25][O:26][C:27]1[CH:28]=[C:29]([C:37]([OH:39])=O)[C:30]2[N:34]=[C:33]([CH3:35])[NH:32][C:31]=2[CH:36]=1.[NH2:40][C:41]1[CH:46]=[CH:45][C:44]([CH3:47])=[CH:43][N:42]=1.CCN(C(C)C)C(C)C>CN(C=O)C.O>[CH3:47][C:44]1[CH:45]=[CH:46][C:41]([NH:40][C:37]([C:29]2[C:30]3[N:34]=[C:33]([CH3:35])[NH:32][C:31]=3[CH:36]=[C:27]([O:26][CH3:25])[CH:28]=2)=[O:39])=[N:42][CH:43]=1

Participants

7

Reactant 4

HCID 153482-Amino-5-methylpyridineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59559998HCID 59559998, compound

Product 1

HCID 59559959HCID 59559959, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

HATU (431 mg, 1.13 mmol) was added to a mixture of 6-methoxy-2-methyl-1H-benzoimidazole-4-carboxylic acid (350 mg, 1.0 mmol), 2-amino-5-picoline (134 mg, 1.24 mmol), and DIEA (0.359 mL, 2.06 mmol) in DMF (5 mL) while stirring at room temperature. The resulting mixture was stirred at room temperature under N2 atmosphere for 16 hours. The mixture was worked up with water and extracted into chloroform; the organic layer was dried over MgSO4, concentrated. The crude product was purified by flash silicagel chromatography (ISCO) eluting with CHCl3:MeOH (95:5) to gain 85 mg light brown color solid product in 27% yield. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.68 (s, 1 H) 12.41 (s, 1 H) 8.27 (d, J=8.56 Hz, 1 H) 8.23 (s, 1 H) 7.68 (dd, J=8.56, 1.76 Hz, 1 H) 7.51 (d, J=2.27 Hz, 1 H) 7.23 (d, J=2.27 Hz, 1 H) 3.85 (s, 3 H) 2.61 (s, 3 H) 2.29 (s, 3 H). LRMS for C16H16N4O2 m/z 297 (M+H)+.

Workup

  1. stirringThe resulting mixture was stirred at room temperature under N2 atmosphere for 16 hours
  2. extractionextracted into chloroform
  3. dry with materialthe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified by flash silicagel chromatography (ISCO)
  6. washeluting with CHCl3:MeOH (95:5)

Sources & evidence

ORD record
ord-33ace2a7508f46d081b3912395bf7952
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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