(R)-2-(tetrazolo[1,5-a]pyrid 6-yl)oxirane → HCID 15137737, compound

HRID 1086475Notes

Reaction equation

HRID 1086475 reaction equation
[N:1]1[N:2]=[N:3][N:4]2[CH:9]=[C:8]([C@@H:10]3[CH2:12][O:11]3)[CH:7]=[CH:6][C:5]=12.[CH3:13][C@H:14]([NH2:27])[CH2:15][C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([O:25][CH3:26])[CH:23]=2)[NH:18][CH:17]=1>CO>[CH3:13][C@H:14]([NH:27][CH2:12][C@@H:10]([C:8]1[CH:7]=[CH:6][C:5]2[N:4]([N:3]=[N:2][N:1]=2)[CH:9]=1)[OH:11])[CH2:15][C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([O:25][CH3:26])[CH:23]=2)[NH:18][CH:17]=1

Participants

4

Reactant 2

HCID 13090314(R)-2-(tetrazolo[1,5-a]pyrid 6-yl)oxiraneHCID 14083211(αS)-5-Methoxy-α-methyl-1H-indole-3-ethanamine

Product 1

HCID 15137737HCID 15137737, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 350 mg of (R)-2-(tetrazolo[1,5-a]pyrid-6-yl)oxirane and 429 mg of (S)-1-methyl-2-(5-methoxy-1H-indol-3-yl)ethyl amine (R. A. Glennon et al., Biol. Psychiatry, 18, 493 (1983) in 8 ml of methanol was heated at reflux under nitrogen for 20 hours. The reaction mixture was concentrated under reduced pressure and the residue (765 mg) was purified twice by preparative TLC on silica gel (95:5:0.5 CH2Cl2 :MeOH:NH4OH) to give 419 mg of (R)-α-[[(1(S)-methyl-2-(5-methoxy-1H-indol-3-yl)ethyl)amino]methyl]tetrazolo[1,5-a]pyridine-6-methanol.

Workup

  1. temperatureat reflux under nitrogen for 20 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue (765 mg) was purified twice by preparative TLC on silica gel (95:5:0.5 CH2Cl2 :MeOH:NH4OH)

Sources & evidence

ORD record
ord-9a80d5e6b43940fdbaa3f8a949c4398e
Source dataset
uspto-grants-1991_07
Patent number
US05030640

Reaction notes

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