Water → HCID 66920647, compound

HRID 1364527Notes

Reaction equation

HRID 1364527 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH2:10][CH:11]([CH3:13])[CH3:12])[N:5]=[C:4]([NH2:14])[CH:3]=1.N1C=CC=CC=1.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH2:29][C:30](Cl)=[O:31])[CH:26]=[CH:27][CH:28]=1.O>C(Cl)Cl>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH2:10][CH:11]([CH3:12])[CH3:13])[N:5]=[C:4]([NH:14][C:30](=[O:31])[CH2:29][C:25]2[CH:26]=[CH:27][CH:28]=[C:23]([O:22][CH3:21])[CH:24]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 27332463-Methoxyphenylacetyl chlorideHCID 66920870HCID 66920870, compound

Product 1

HCID 66920647HCID 66920647, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 20 mg (0.11 mmol) of 4,6-diamino-2-isobutyl-nicotinonitrile in 1 mL of CH2Cl2 was added 40 μL (0.49 mmol) of pyridine, then 30 μL (0.19 mmol) of (3-methoxyphenyl)acetyl chloride. The solution was stirred at ambient temperature for 10 minutes then 0.5 mL of water was added. The mixture was concentrated under reduced pressure, then the residue was taken up in 5 mL of ethyl acetate and extracted with water (2×2 mL), saturated NaHCO3(aq.), and brine (1×2 mL), dried over MgSO4, filtered, and concentrated to an oil. The product was partially purified via silica gel chromatography, eluting with 30% ethyl acetate:hexanes to provide a solid. This was recrystallized from methanol to provide 8 mg (23%) of a white solid. 1H NMR (300 MHz, d6-DMSO) δ 10.48 (s, 1H), 7.37 (s, 1H), 7.22 (t, 1H, J=7.8 Hz), 6.84 (m, 5H), 3.73 (s, 3H), 3.66 (s, 2H), 2.54 (d, 2H, J=7.1 Hz), 2.09 (m, 1H), 0.92 (d, 6H, J=6.1 Hz); MS (ESI) m/e 339 (M+H)+, 337 (M−H)−.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. extractionextracted with water (2×2 mL), saturated NaHCO3(aq.), and brine (1×2 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to an oil
  6. customThe product was partially purified via silica gel chromatography
  7. washeluting with 30% ethyl acetate
  8. customhexanes to provide a solid
  9. customThis was recrystallized from methanol

Sources & evidence

ORD record
ord-86247c6abe394cf1be310f9616c01ef2
Source dataset
uspto-grants-2011_02
Patent number
US07888374B2

Reaction notes

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