Water → HCID 11652380, compound

HRID 1364518Notes

Reaction equation

HRID 1364518 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([O:10][CH2:11][CH3:12])[N:5]=[C:4]([NH2:13])[CH:3]=1.[S:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[CH2:19][C:20](Cl)=[O:21].O>N1C=CC=CC=1>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([O:10][CH2:11][CH3:12])[N:5]=[C:4]([NH:13][C:20](=[O:21])[CH2:19][C:15]2[S:14][CH:18]=[CH:17][CH:16]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1623622-Thiopheneacetyl chlorideHCID 131498684,6-Diamino-2-ethoxypyridine-3-carbonitrile

Product 1

HCID 11652380HCID 11652380, compoundYield 9.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 50 mg (0.28 mmol) of 4,6-diamino-2-ethoxy-nicotinonitrile in 1 mL of pyridine was added 150 μL (1.21 mmol) of 2-thiopheneacetyl chloride, dropwise. The mixture was stirred for 5 min at ambient temperature, then 1 mL of water was added. The mixture was stirred for an additional 30 minutes then concentrated under reduced pressure. The residue was taken up in 10 mL of ethyl acetate, extracted with water (2×5 mL), 1M HCl(aq.) (1×5 mL), saturated NaHCO3(aq.) (2×5 mL), and brine (1×5 mL), dried over MgSO4, filtered, and concentrated to an oil. This was partially purified via silica gel chromatography, eluting with 30% ethyl acetate:hexanes to provide a sticky, yellow solid. This was triturated with methanol to provide 8 mg (9%) of a white solid. 1H NMR (300 MHz, d6-DMSO) δ 10.33 (s, 1H), 7.38 (m, 1H), 7.18 (s, 1H), 6.97 (m, 2H), 6.92 (s, 2H), 4.34 (q, 2H, J=7.1 Hz), 3.94 (s, 2H), 1.30 (t, 3H, J=7.1 Hz); MS (ESI) m/e=275 (M−Et+H)+, 303 (M+H)+, 301 (M−H)−.

Workup

  1. stirringThe mixture was stirred for an additional 30 minutes
  2. concentrationthen concentrated under reduced pressure
  3. extractionextracted with water (2×5 mL), 1M HCl(aq.) (1×5 mL), saturated NaHCO3(aq.) (2×5 mL), and brine (1×5 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to an oil
  7. customThis was partially purified via silica gel chromatography
  8. washeluting with 30% ethyl acetate
  9. customhexanes to provide a sticky, yellow solid
  10. customThis was triturated with methanol

Sources & evidence

ORD record
ord-93efc72db1a947e88696b6d0943ad247
Source dataset
uspto-grants-2011_02
Patent number
US07888374B2

Reaction notes

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