Ethyl cyanoacetate → HCID 90438206, compound

HRID 924211Notes

Reaction equation

HRID 924211 reaction equation
[F:1][C:2]([F:24])([F:23])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=3)=[N:11]2)=[CH:6][CH:5]=1.[C:25]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])#[N:26].N1CCCC1>C(O)C>[C:25](/[C:27](=[CH:19]/[C:18]1[CH:21]=[CH:22][C:15]([C:12]2[N:13]=[CH:14][N:10]([C:7]3[CH:8]=[CH:9][C:4]([O:3][C:2]([F:23])([F:1])[F:24])=[CH:5][CH:6]=3)[N:11]=2)=[CH:16][CH:17]=1)/[C:28]([O:30][CH2:31][CH3:32])=[O:29])#[N:26]

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 31268PyrrolidineHCID 578244624-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzaldehyde

Product 1

HCID 90438206HCID 90438206, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To 4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzaldehyde (3.0 g, 9.0 mmol) in ethanol (11.5 mL) was added ethyl 2-cyanoacetate (0.95 mL, 8.9 mmol) and pyrrolidine (0.97 mL, 12 mmol). A yellow precipitate formed immediately and additional ethanol (10 mL) was added. The reaction was stirred at room temperature for 18 hours and then concentrated onto Celite®. Purification by flash column chromatography using 0-100% ethyl acetate/B, where B=1:1 dichloromethane/hexanes as eluent afforded the title compound as a white solid (2.1 g, 50%): 1H NMR (400 MHz, CDCl3) δ 8.61 (s, 1H), 8.36-8.31 (m, 2H), 8.29 (s, 1H), 8.12 (d, J=8.4 Hz, 2H), 7.85-7.79 (m, 2H), 7.41 (d, J=8.3 Hz, 2H), 4.41 (q, J=7.1 Hz, 2H), 1.42 (t, J=7.1 Hz, 3H); 13C NMR (101 MHz, CDCl3) δ 162.46, 162.24, 154.18, 141.89, 135.36, 134.76, 132.41, 131.53, 127.22, 122.47, 121.33, 115.51, 103.28, 62.82, 14.19; ESIMS m/z 429 ([M+H]+).

Workup

  1. customA yellow precipitate formed immediately
  2. concentrationconcentrated onto Celite®
  3. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-b35f4ea5445b423a8bb8c15d8d98783f
Source dataset
uspto-grants-2016_03
Patent number
US09278964B2

Reaction notes

Loading…