(R)-2-(tetrazolo[1,5-a]pyrid 6-yl)oxirane → HCID 15137741, compound

HRID 1086477Notes

Reaction equation

HRID 1086477 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][CH:14]([NH2:33])[CH2:15][C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:23]=2)[NH:18][CH:17]=1>C(O)C>[CH3:13][C@@H:14]([NH:33][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][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:23]=2)[NH:18][CH:17]=1.[CH3:13][C@H:14]([NH:33][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][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:23]=2)[NH:18][CH:17]=1

Participants

5

Reactant 2

HCID 13090314(R)-2-(tetrazolo[1,5-a]pyrid 6-yl)oxiraneHCID 151377401-methyl-2-(5-benzyloxy-1H-indol-3-yl)ethyl amine

Product 2

HCID 15137741HCID 15137741, compoundHCID 15137742HCID 15137742, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3.24 g of (R)-2-(tetrazolo-[1,5-a]pyrid-6-yl)oxirane and 5.89 g of 1-methyl-2-(5-benzyloxy-1H-indol-3-yl)ethyl amine in 84 ml of absolute ethanol was heated at reflux under nitrogen for 24 hours. The reaction mixture was concentrated and the residue purified by preparative TLC on silica gel (95:5:0.5 CH2Cl2 :MeOH:NH4OH) to give 1.29 g of (R)-α-[[(1(R)-methyl-2-(5-benzyloxy-1H-indol-3-yl)ethyl)amino]methyl]tetrazolo[1,5-a]pyridine-6-methanol and 1.46 g of (R)-α-[[(1(S)-methyl-2-(5-benzyloxy-1H-indol-3-yl)ethyl)-amino]methyl]tetrazolo[1,5-a]pyridine-6-methanol.

Workup

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

Sources & evidence

ORD record
ord-044c0e56d7894c52a50dd9f602090ce0
Source dataset
uspto-grants-1991_07
Patent number
US05030640

Reaction notes

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