Hydrochloric Acid → HCID 178509414, compound

HRID 2401812Notes

Reaction equation

HRID 2401812 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:12]1[C:13]([C:34]#[N:35])=[C:14]([C:28]2[CH:33]=[CH:32][N:31]=[N:30][CH:29]=2)[S:15][C:16]=1[C:17]1[N:21]=[CH:20][N:19](C2CCCCO2)[N:18]=1.CO.Cl.O>>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:12]1[C:13]([C:34]#[N:35])=[C:14]([C:28]2[CH:33]=[CH:32][N:31]=[N:30][CH:29]=2)[S:15][C:16]=1[C:17]1[NH:21][CH:20]=[N:19][N:18]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 962WaterHCID 667490584-(2-Naphthylmethyl)-2-pyridazin-4-yl-5-[1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl]thiophene-3-carbonitrile

Product 1

HCID 178509414HCID 178509414, compoundYield 60.3%

Conditions

Temperature
50 °C

Procedure

4-(2-Naphthylmethyl)-2-pyridazin-4-yl-5-[1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl]thiophene-3-carbonitrile (0.03178 g, 0.06641 mmol) was dissolved in methanol (3.00 mL, 74.0 mmol). HCl in water (12 M, 3.00 mL, 36.0 mmol) was added. The solution was heated at 50° C. for 60 min then cooled to rt. The mixture was evaporated in vacuo to remove the most of methanol. To the residue was added 30 mL saturated sodium bicarbonate solution, extracted with 40 mL ethyl acetate twice. The combined EtOAc layers were washed with 20 mL water then concentrated in vacuo. The resulting crystalline solid was collected by filtration to afford a pure product (0.0158 g, yield 60.3%). LCMS: (AA) ES+ 395. 1H NMR (300 MHz, d4-methanol) δ: 9.60 (s, 1H), 9.27-9.29 (m, 1H), 8.47 (s, 1H), 8.09-8.11 (m, 1H), 7.69-7.77 (m, 4H), 7.37-7.47 (m, 3H), 3.30 (s, 2H).

Workup

  1. temperaturethen cooled to rt
  2. customThe mixture was evaporated in vacuo
  3. customto remove the most of methanol
  4. additionTo the residue was added 30 mL saturated sodium bicarbonate solution
  5. extractionextracted with 40 mL ethyl acetate twice
  6. washThe combined EtOAc layers were washed with 20 mL water
  7. concentrationthen concentrated in vacuo
  8. filtrationThe resulting crystalline solid was collected by filtration

Sources & evidence

ORD record
ord-57a82bce5a23451589210dd11e8ae54b
Source dataset
uspto-grants-2014_08
Patent number
US08796268B2

Reaction notes

Loading…