Triethylamine → HCID 178521744, compound

HRID 1797152Notes

Reaction equation

HRID 1797152 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([CH:7]2[CH2:10][CH2:9]C2)[CH:3]=1.ClC(Cl)(Cl)[C:13]([C:15]1[NH:16][CH:17]=[CH:18][CH:19]=1)=[O:14].C(N(CC)CC)C>C(#N)C>[CH:7]1([C:4]2[CH:3]=[C:2]([NH:1][C:13]([C:15]3[NH:16][CH:17]=[CH:18][CH:19]=3)=[O:14])[NH:6][N:5]=2)[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3214872-(Trichloroacetyl)pyrroleHCID 178507267HCID 178507267, compound

Product 1

HCID 178521744HCID 178521744, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 260 mg (1.9 mmol) of 5-amino-3-cyclobutylpyrazole in 7 mL of acetonitrile was added 407 mg (1.9 mmol) of 2-trichloroacetylpyrrole and 220 μL of triethylamine. The mixture was stirred and heated at reflux, under nitrogen, for 12 hours. TLC analysis showed some starting material still remained. The mixture was concentrated and chromatographed over silica gel, eluting with 5% methanol in chloroform. The fractions containing the product were concentrated to an oil, which crystallized upon concentration from ether and methanol, to afford 200 mg (0.87 mmol, 46%) of a beige solid, m.p. 207–209° C., 1H NMR (DMSO-d6) δ 12.1 (s, 1H), 11.5 (s, 1H), 10.2 (s, 1H), 7.08 (s, 1H), 6.89 (s, 1H), 6.41 (s, 1H), 6.09 (s, 1H), 3.46 (m, 1H), 2.24 (m, 2H), 2.11 (m, 2H), 2.0–1.8 (m, 2H); IR (drift) 3329, 3294, 3257, 3225 (b), 2460 (w), 2351 (w), 2318 (w), 2257 (w), 1643 (s), 1588 (s), 1541, 1487 (s), 1416, 757, 747, cm−1 Anal. Calcd for C12H14N4O: C, 62.59; H, 6.13; N, 24.33. Found: C, 62.37; H, 6.22; N, 24.13.

Workup

  1. temperatureheated
  2. temperatureat reflux, under nitrogen, for 12 hours
  3. concentrationThe mixture was concentrated
  4. customchromatographed over silica gel
  5. washeluting with 5% methanol in chloroform
  6. additionThe fractions containing the product
  7. concentrationwere concentrated to an oil, which
  8. customcrystallized upon concentration from ether and methanol

Sources & evidence

ORD record
ord-2d53974e996b49af830bbbdc1682daac
Source dataset
uspto-grants-2006_04
Patent number
US07034049B1

Reaction notes

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