Triethylamine → HCID 178490638, compound

HRID 538815Notes

Reaction equation

HRID 538815 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:26][CH3:27])=[C:6]([CH:25]=1)[C:7](=S)/[N:8]=[C:9]1\[S:10][C:11]2[C:21]([CH3:23])([CH3:22])[O:20][CH2:19][CH2:18][C:12]=2[N:13]\1[CH2:14][CH:15]([CH3:17])[CH3:16].C(N(CC)CC)C.[N:35]#[C:36][NH2:37]>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:26][CH3:27])=[C:6]([C:7](=[N:37][C:36]#[N:35])/[N:8]=[C:9]2\[S:10][C:11]3[C:21]([CH3:23])([CH3:22])[O:20][CH2:19][CH2:18][C:12]=3[N:13]\2[CH2:14][CH:15]([CH3:17])[CH3:16])[CH:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9864CyanamideHCID 178490710HCID 178490710, compound

Product 1

HCID 178490638HCID 178490638, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of Example 89H (0.18 g, 0.42 mmol) in acetonitrile (10 mL) were added mercuric acetate (0.18 g, 0.55 mmol, Aldrich), triethylamine (0.18 mL, 1.27 mmol) and cyanamide (0.04 g, 0.85 mmol, Aldrich). After stirring at 80° C. for 16 hr, the reaction mixture was cooled and quenched with saturated NaHCO3 (20 mL). The aqueous layer was extracted with ethyl acetate (3×20 mL). The combined the organic extracts were washed with water (1×25 mL), dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-50% ethyl acetate in hexanes) and followed by crystallization from ethyl acetate/hexanes to afford 0.04 g (21%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.86 (d, J=6.8 Hz, 6H), 1.51 (s, 6H), 2.06-2.35 (m, 1H), 2.66-2.87 (m, 2H), 3.81 (s, 3H), 3.94-4.14 (m, 4H), 7.21 (d, J=9.2 Hz, 1H), 7.33 (d, J=2.4 Hz, 1H), 7.52 (dd, J=9.2, 2.7 Hz, 1H); MS (ESI+) m/z 433 (M+H)+; Anal. Calculated C21H25ClN4O2S: C, 58.25; H, 5.82; N, 12.94. Found: C, 58.30; H, 5.79; N, 12.64.

Workup

  1. temperaturethe reaction mixture was cooled
  2. customquenched with saturated NaHCO3 (20 mL)
  3. extractionThe aqueous layer was extracted with ethyl acetate (3×20 mL)
  4. washwere washed with water (1×25 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography
  9. customfollowed by crystallization from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-8e0e573171844d6d90f591641a91a5dd
Source dataset
uspto-grants-2014_10
Patent number
US08865753B2

Reaction notes

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