Methanol → HCID 178419531, compound

HRID 1587522Notes

Reaction equation

HRID 1587522 reaction equation
[CH2:1]([C:3]1[N:12]=[C:11]([CH2:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[CH:5]=[C:6]([O:34]C)[C:7](=[O:33])[N:8]2[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]2[NH:32][N:31]=[N:30][N:29]=2)=[CH:18][CH:17]=1)[CH3:2].B(Br)(Br)[Br:37].CO>ClCCl>[BrH:37].[CH2:1]([C:3]1[N:12]=[C:11]([CH2:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[CH:5]=[C:6]([OH:34])[C:7](=[O:33])[N:8]2[CH2:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]2[NH:32][N:31]=[N:30][N:29]=2)=[CH:20][CH:21]=1)[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 178435382HCID 178435382, compound

Product 1

HCID 178419531HCID 178419531, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5,7-Diethyl-3-methoxy-1-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl]-1,6-naphthyridin-2(1H)-one (80 mg) was suspended in dichloromethane (1 ml) and a 1M solution of boron tribromide in dichloromethane (0.5 ml) was added. The mixture was stirred for 16 hours then methanol (3 ml) was added dropwise. The mixture was heated at reflux for 5 minutes and volatile material was then removed by evaporation. The residue was recrystallised from ethanol/ether to give 5,7-diethyl-3-hydroxy-1-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)-methyl]-1,6-naphthyridin-2(1H)-one hydrobromide as a solid (45 mg), m.p. 190°-194° C.; NMR (d6 -DMSO): 1.24(t, 3H), 1.30(t, 3H), 2.92(q, 2H), 3.22(q, 2H), 5.64(s, 2H), 7.07(d, 2H), 7.22(d, 2H), 7.45-7.75(m, 6H); mass spectrum (+ve FAB, methanol/NBA): 453 (M+H)+ ; microanalysis, found: C, 57.1; H, 4.9; N, 14.7%; C26H24N6O2.Hbr.1.5H2O requires: C, 56.7; H, 5.1; N, 15.2%.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 5 minutes
  3. customvolatile material was then removed by evaporation
  4. customThe residue was recrystallised from ethanol/ether

Sources & evidence

ORD record
ord-0850bb0980d34ae1b2617fd3c566cfa6
Source dataset
uspto-grants-1993_06
Patent number
US05217976

Reaction notes

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