2-Amino-5-methylpyridine → HCID 59279506, compound

HRID 1098091Notes

Reaction equation

HRID 1098091 reaction equation
C(Cl)(=O)C(Cl)=O.[O:7]=[C:8]1[O:12][CH:11]([C:13]([OH:15])=O)[CH2:10][CH2:9]1.CCN(C(C)C)C(C)C.[NH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][N:27]=1>C(Cl)Cl.CN(C=O)C.O>[CH3:32][C:29]1[CH:30]=[CH:31][C:26]([NH:25][C:13]([CH:11]2[CH2:10][CH2:9][C:8](=[O:7])[O:12]2)=[O:15])=[N:27][CH:28]=1

Participants

8

Reactant 4

HCID 153482-Amino-5-methylpyridineHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 2515245-Oxo-2-tetrahydrofurancarboxylic acid

Product 1

HCID 59279506HCID 59279506, compoundYield 38%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent3×

Procedure

Oxalyl chloride (0.252 g, 1.63 mmol) in DCM (5 mL) was added slowly to a stirred solution of 5-oxotetrahydrofuran-2-carboxylic acid (Step 1) (0.215 g, 1.65 mmol) in DCM (10 ml) and DMF (50 μl) at 0° C. After 3 hrs at ambient temperature, gas evolution had subsided. DIPEA (0.64, 4.95 mmol) was added followed by the addition of 2-amino-5-picoline (0.357 g, 3.3 mmol) in DCM (5 mL). The reaction mixture was kept at ambient temperature for 3 hrs. Water (0.5 mL) was added and the reaction mixture was concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluting with a gradient consisting of 0-40% MeOH in DCM) to give the title compound as a colorless oil (0.138 g). 1H NMR (500 MHz, CDCl3) δ 8.74 (br s, 1H), 8.13 (d, 1H), 8.08 (d, 1H), 7.54 (dd, 1H), 4.99 (t, 1H), 2.71 (m, 1H), 2.63 (m, 2H), 2.48 (m, 1H), 2.31 (s, 3H).

Workup

  1. waitThe reaction mixture was kept at ambient temperature for 3 hrs
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customThe residue was purified by column chromatography (silica gel
  4. washeluting with a gradient

Sources & evidence

ORD record
ord-99ec0f537e5b495b9daa5d39b525667b
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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