Water → HCID 13189822, compound

HRID 1979697Notes

Reaction equation

HRID 1979697 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1.[CH3:13][N:14]1[C:18]([NH:19][CH2:20][CH2:21][CH2:22][O:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([CH2:30][N:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)[CH:25]=2)=[N:17][C:16]([CH:37]=[O:38])=[N:15]1.O>CCOCC.O1CCCC1>[CH3:13][N:14]1[C:18]([NH:19][CH2:20][CH2:21][CH2:22][O:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([CH2:30][N:31]3[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]3)[CH:25]=2)=[N:17][C:16]([CH:37]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[OH:38])=[N:15]1

Participants

7

Reactant 4

HCID 962WaterHCID 79732-BromopyridineHCID 12774364HCID 12774364, compoundHCID 178418339Butyllithium

Product 1

HCID 13189822HCID 13189822, compoundYield 102.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

n-Butyllithium (1.6M in n-hexane, 8.12 ml) was added dropwise during 15 min to a stirred solution of 2-bromopyridine (1.86 g, 1.12 ml) in anhydrous ether (10 ml) at -70°, under nitrogen. The brown solution was stirred at -70° for 0.5 h before a solution of 1-methyl-5-[[3-[3-(1-piperidinylmethyl)phenoxy]propyl]amino]-1H-1,2,4-triazole-3-carboxaldehyde (2.0 g) in anhydrous tetrahydrofuran (20 ml) was added dropwise at -70° and the solution was stirred at -40° for 2 h before water (20 ml) was added and the mixture was allowed to stand overnight at 20°. The mixture was concentrated extracted with ethyl acetate and the extract was dried and evaporated to give an oil (2.5 g) which was chromatographed using System C as eluent to give a solid (0.48 g). This was crystallised from ethyl acetate to give the title compound (0.25 g) as a white powder m.p. 152°-154° (d).

Workup

  1. additionwas added dropwise at -70°
  2. additionwas added
  3. concentrationThe mixture was concentrated
  4. extractionextracted with ethyl acetate
  5. customthe extract was dried
  6. customevaporated

Sources & evidence

ORD record
ord-5f0735c17819421da10bc780994fd20e
Source dataset
uspto-grants-1984_11
Patent number
US04482552

Reaction notes

Loading…