Triethylamine → HCID 178453335, compound

HRID 2399704Notes

Reaction equation

HRID 2399704 reaction equation
[NH:1]1[C:5]([CH2:6][C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][CH:11]=[C:10]3[CH2:16][CH2:17][NH2:18])=[N:4][N:3]=[N:2]1.C(N(CC)CC)C.[O:26](C(OC(C)(C)C)=O)[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=O>C(Cl)Cl>[C:30]([O:29][C:27]([NH:18][CH2:17][CH2:16][C:10]1[C:9]2[C:13](=[CH:14][CH:15]=[C:7]([CH2:6][C:5]3[NH:1][N:2]=[N:3][N:4]=3)[CH:8]=2)[NH:12][CH:11]=1)=[O:26])([CH3:33])([CH3:32])[CH3:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 178510860HCID 178510860, compound

Product 1

HCID 178453335HCID 178453335, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 2-(5-tetrazol-5-ylmethyl-1H-indol-3-yl)ethylamine (1.76 g, 7.27 mmol) in dry CH2Cl2 (40 ml) was added triethylamine (1.5 g, 14.9 mmol) and (BOC)2O (1.9 g, 7.3 mmol) and the mixture stirred for 16 h. The solvent was removed under vacuum and the residue chromatographed on silica-gel eluting with EtOH/Et2O/H2O/NH3 (20:60:8:1) to give the title product (1.6 g, 64%); δ (360 MHz, CD3OD) 1.41 (9H, s, 3 of CH3); 2.87 (2H, t, J=7.4 Hz, CH2); 3.30 (2H, t, J=7.4 Hz, CH2); 4.32 (2H, s, CH2); 6.99 (1H, d, J=8.3 Hz, Ar--H); 7.04 (1H, s, Ar--H); 7.26 (1H, d, J=8.3 Hz, Ar--H); 7.49 (1H, s, Ar--H).

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue chromatographed on silica-gel
  3. washeluting with EtOH/Et2O/H2O/NH3 (20:60:8:1)

Sources & evidence

ORD record
ord-31f7e99d76e14402b6f2265a1ac85d51
Source dataset
uspto-grants-1995_09
Patent number
US05451588

Reaction notes

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