Hydrochloric Acid → HCID 178470537, compound

HRID 843168Notes

Reaction equation

HRID 843168 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][CH2:18][CH2:19][NH2:20])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].[N+]([O-])(O)=O.CC1C=C(C)[N:28]([C:32](=N)[NH2:33])N=1.C(N(CC)CC)C.[ClH:42]>CN(C=O)C.C(O)C>[ClH:42].[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][CH2:18][CH2:19][NH:20][C:32]([NH2:33])=[NH:28])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 1981863,5-Dimethyl-1H-pyrazole-1-carboxamidine mononitrateHCID 510558HCID 510558, compound

Product 1

HCID 178470537HCID 178470537, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(3-amino-propoxy)-3-methyl-benzofuran-2-carboxylic acid ethyl ester (the compound in Example 109-a: 10 mg), 3,5-dimethyl-1-guanylpyrazole nitrate (14 mg) and triethylamine (100 μl) in DMF (1 ml) was stirred at 40° C. for two days. The solvent was removed under a reduced pressure and the residue was purified by reversed phase column chromatography using Sep-Pak Cartridge C18 (Waters) (H2O-MeOH) to give a white powder. The powder was dissolved in a solution of 1N HCl (0.3 ml) and ethanol (5 ml), and the solution was concentrated in vacuo to give 4-(3-guanidino-propoxy)-3-methyl-benzofuran-2-carboxylic acid ethyl ester hydrochloric acid salt (9 mg) as a white powder. FAB-MS: m/z 320 (MH+); 1H-NMR (CD3OD): δ 1.40 (3H, t, J=7 Hz), 2.18 (2H, quintet, J=6.5 Hz), 2.75 (3H, s), 3.46 (2H, t, J=7 Hz), 4.22 (2H, t, J=6 Hz), 4.39 (2H, q, J=7 Hz), 6.78 (1H, d, J=8 Hz), 7.10 (1H, d, J=8 Hz), 7.39 (1H, t, J=8 Hz).

Workup

  1. customThe solvent was removed under a reduced pressure
  2. customthe residue was purified by reversed phase column chromatography
  3. custom(Waters) (H2O-MeOH) to give a white powder
  4. concentrationthe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-f873b4542b9b4b10a743725cf63642ff
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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