5-METHOXY-alpha,alpha-DIMETHYL-1H-INDOL-3-YL-ETHANEAMINE → (R)-alpha-[[(1,1-dimethyl-2-(5-methoxy-1H-indol-3-yl)ethyl)amino]methyl]tetrazolo[1,5-a]pyridine-6-methanol

HRID 1086470Notes

Reaction equation

HRID 1086470 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:14]([NH2:28])([CH3:27])[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>C(O)C>[CH3:27][C:14]([NH:28][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])([CH3:13])[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 126196645-METHOXY-alpha,alpha-DIMETHYL-1H-INDOL-3-YL-ETHANEAMINEHCID 13090314(R)-2-(tetrazolo[1,5-a]pyrid 6-yl)oxirane

Product 1

HCID 15137726(R)-alpha-[[(1,1-dimethyl-2-(5-methoxy-1H-indol-3-yl)ethyl)amino]methyl]tetrazolo[1,5-a]pyridine-6-methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 598 mg of (R)-2-(tetrazolo[1,5-a]pyrid-6-yl)oxirane and 782 mg of (1,1-dimethyl-2-(5-methoxy-1H-indol-3-yl)ethyl amine (B. Heath-Brown and P. G. Philpott, J. Chem. Soc., 7165 (1965)) in 12 ml of absolute ethanol was heated at reflux for 44 hours. The reaction mixture was concentrated and the residue (1.15 g) was chromatographed on silica gel (95:5:0.5 CH2Cl2 :MeOH:NH4OH) to give 0.997 g of (R)-α-[[(1,1-dimethyl-2-(5-methoxy-1H-indol-3-yl)ethyl)amino]methyl]tetrazolo[1,5-a]pyridine-6-methanol.

Workup

  1. temperatureat reflux for 44 hours
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue (1.15 g) was chromatographed on silica gel (95:5:0.5 CH2Cl2 :MeOH:NH4OH)

Sources & evidence

ORD record
ord-e48852750c6545d2a70cc3181b0c1708
Source dataset
uspto-grants-1991_07
Patent number
US05030640

Reaction notes

Loading…