(R)-2-(tetrazolo[1,5-a]pyrid 6-yl)oxirane → (R)-alpha-[[(1(R)-methyl-2-(5-methoxy-1H-indol-3-yl)ethyl)amino]methyl]tetrazolo[1,5-a]pyridine-6-methanol

HRID 1086474Notes

Reaction equation

HRID 1086474 reaction equation
[CH3:1][C@@H:2]([NH2:15])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[NH:6][CH:5]=1.[N:16]1[N:17]=[N:18][N:19]2[CH:24]=[C:23]([C@@H:25]3[CH2:27][O:26]3)[CH:22]=[CH:21][C:20]=12>CO>[CH3:1][C@@H:2]([NH:15][CH2:27][C@@H:25]([C:23]1[CH:22]=[CH:21][C:20]2[N:19]([N:18]=[N:17][N:16]=2)[CH:24]=1)[OH:26])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[NH:6][CH:5]=1

Participants

4

Reactant 2

HCID 13090314(R)-2-(tetrazolo[1,5-a]pyrid 6-yl)oxiraneHCID 14083212(2R)-1-(5-methoxyindol-3-yl)prop-2-ylamine

Product 1

HCID 15137736(R)-alpha-[[(1(R)-methyl-2-(5-methoxy-1H-indol-3-yl)ethyl)amino]methyl]tetrazolo[1,5-a]pyridine-6-methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 553 mg of partially resolved (R)-1-methyl-2-(5-methoxy-1H-indol-3-yl)ethyl amine (R. A. Glennor et al, Biol Psychiatry, 18,493 (1983) and 452 mg of (R)-2-(tetrazolo[1,5-a]pyrid-6-yl)oxirane in 10 ml of methanol under nitrogen was heated at reflux for 24 hours. The reaction mixture was concentrated under reduced pressure and the residue (1.0 g) purified by careful preparative TLC on silica gel (95:5:0.5 CH2Cl2 :MeOH:NH4OH) to give 515 mg of (R)-α-[[(1(R)-methyl-2-(5-methoxy-1H-indol-3-yl)ethyl)amino]methyl]tetrazolo[1,5-a]pyridine-6-methanol plus 11.6 mg of the adduct resulting from the small amount of (S)-amine present in the starting material.

Workup

  1. temperatureat reflux for 24 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue (1.0 g) purified by careful preparative TLC on silica gel (95:5:0.5 CH2Cl2 :MeOH:NH4OH)

Sources & evidence

ORD record
ord-e1a8bc4e16934c5cb0c6df2a023c5ff3
Source dataset
uspto-grants-1991_07
Patent number
US05030640

Reaction notes

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