HCID 178441629, compound → HCID 178441631, compound

HRID 719559Notes

Reaction equation

HRID 719559 reaction equation
[CH2:1]([C:5]1[N:9]=[C:8]([CH2:10][CH2:11][CH2:12][NH:13]C(OC(C)(C)C)=O)[N:7]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]3[NH:38][N:37]=[N:36][N:35]=3)=[CH:24][CH:23]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4]>Cl.O1CCOCC1>[CH2:1]([C:5]1[N:9]=[C:8]([CH2:10][CH2:11][CH2:12][NH2:13])[N:7]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]3[NH:38][N:37]=[N:36][N:35]=3)=[CH:24][CH:23]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 178441629HCID 178441629, compound

Product 1

HCID 178441631HCID 178441631, compoundYield 106.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Under a static nitrogen atmosphere 2.40 g (4.7 mmol) of 5-[4′-[[3-butyl-5-(N-Boc-3-aminopropyl)-1H-1,2,4-triazol-1-yl]methyl][1,1′-biphenyl]-2-yl]-1H-tetrazole from Example 67 was dissolved in 30 mL of 4N HCl in dioxane at ambient temperature and allowed to stir overnight. The solvents were removed in vacuo; the residue was triturated with diethyl ether and filtered providing 2.08 g (98%) of 5-[4′-[[3-butyl-5-(3-aminopropyl)-1H-1,2,4-triazol-1-yl]methyl][1,1′-biphenyl]-2-yl]-1H-tetrazole as the hydrochloride salt: NMR (DMSO-d6) δ 0.88 (t, J=7 Hz, 3H), 1.25–1.39 (m, 2H), 1.57–1.69 (m, 2H), 1.92–2.40 (m, 2H), 2.62 (t, J=7 Hz, 2H), 2.89 (q, J=8 Hz, 2H), 2.98 (t, J=8 Hz, 2H), 5.38 (s, 2H), 7.10 (d, J=8 Hz, 2H), 7.19 (d, J=8 Hz, 2H), 7.54 (d, J=8 Hz, 1H), 7.59 (dd, J=8 and 2 Hz, 1H), 7.66 (s, 1H), 7.70 (dd, J=8 and 2 Hz, 1H), 8.10 (br s, 2H); MS (FAB) m/e (rel intensity) 417 (38), 389 (10), 357 (10), 207 (100), 166 (50), 139 (10) 115 (10); HRMS. Calc'd for M+H: 417.2515. Found: 417.2563.

Workup

  1. customThe solvents were removed in vacuo
  2. customthe residue was triturated with diethyl ether
  3. filtrationfiltered

Sources & evidence

ORD record
ord-bcffd77189474c5b8fbf1f9ab331ab55
Source dataset
uspto-grants-2006_11
Patent number
US07132437B2

Reaction notes

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