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

HRID 1643822Notes

Reaction equation

HRID 1643822 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 (0.359mL, 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-dd659dd80d10404cbb6a9b83e7afea86
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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