Water → HCID 20438214, compound

HRID 1979696Notes

Reaction equation

HRID 1979696 reaction equation
C([Li])CCC.[O:6]1[CH:10]=[CH:9][CH:8]=[CH:7]1.[CH3:11][N:12]1[C:16]([NH:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][N:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)[CH:23]=2)=[N:15][C:14]([CH:35]=[O:36])=[N:13]1.O>O1CCCC1>[O:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[CH:35]([C:14]1[N:15]=[C:16]([NH:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][N:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)[CH:23]=2)[N:12]([CH3:11])[N:13]=1)[OH:36]

Participants

6

Reactant 4

HCID 962WaterHCID 8029FuranHCID 12774364HCID 12774364, compoundHCID 178418339Butyllithium

Product 1

HCID 20438214HCID 20438214, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyllithium (1.55M in n-hexane, 5.96 ml) was added dropwise to a stirred solution of furan (0.16 ml) in anhydrous tetrahydrofuran (20 ml), under nitrogen at -40°. The stirred solution was allowed to warm slowly to 20°, heated under reflux for 3 h, added dropwise at 0° to a solution of 1-methyl-5-[[3-[3-(1-piperidinylmethyl)phenoxy]propyl]amino]-1H-1,2,4-triazole-3-carboxaldehyde (1.0 g) in tetrahydrofuran (10 ml), and the resulting solution was stirred at 20° for 18 h. Water (20 ml) was added, the mixture concentrated, extracted with ethyl acetate and the extract was dried and evaporated. The residual oil (0.9 g) was chromatographed using System C to give the title compound (0.16 g) as a brown oil.

Workup

  1. temperatureto warm slowly to 20°
  2. temperatureheated
  3. temperatureunder reflux for 3 h
  4. concentrationthe mixture concentrated
  5. extractionextracted with ethyl acetate
  6. customthe extract was dried
  7. customevaporated
  8. customThe residual oil (0.9 g) was chromatographed

Sources & evidence

ORD record
ord-d71b476ef6ae41e192878d703f35d344
Source dataset
uspto-grants-1984_11
Patent number
US04482552

Reaction notes

Loading…