HCID 178441767, compound → HCID 178441772, compound

HRID 719557Notes

Reaction equation

HRID 719557 reaction equation
[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[NH:27][N:26]=[N:25][N:24]=3)=[CH:13][CH:12]=2)[N:8]=[C:7]([CH:28](OC)[O:29]C)[N:6]=1)[CH2:2][CH2:3][CH3:4]>C(O)C.Cl>[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[NH:27][N:26]=[N:25][N:24]=3)=[CH:13][CH:12]=2)[N:8]=[C:7]([CH:28]=[O:29])[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 178441767HCID 178441767, compound

Product 1

HCID 178441772HCID 178441772, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A 92 mg sample of 5-[4′-[[5-butyl-3-(dimethoxymethyl)-1H-1,2,4-triazol-1-yl]methyl][1,1′-biphenyl]-2-yl]-1H-tetrazole from Example 24 was dissolved in 20 ml of ethanol and 2 ml of 3N HCl. The reaction was stirred at ambient temperature for 3 days. The solvent was removed in vacuo. Lyophilization from acetonitrile/water gave 70 mg (81%) of 5-butyl-1-[2′-(1H-tetrazol-5-yl)[1,1′-biphenyl]-4-ylmethyl]-1H-1,2,4-triazole-3-carboxaldehyde as the colorless hydrochloride salt: NMR (CDCl3) δ 0.89 (t, J=8 Hz, 3H), 1.30–1.44 (m, 2H), 1.66–1.78 (m, 2H), 2.78 (t, J=8 Hz, 2H), 5.38 (s, 2H), 7.17 (q, J=8 Hz, 4H), 7.40 (d, J=8 Hz, 1H), 7.50–7.64 (m, 2H), 8.02 (d, J=8 Hz, 1H); MS (FAB) m/e (rel intensity) 388 (36), 235 (42), 207 (100), 192 (50); HRMS. Calc'd for M+Li: 395.2046. Found: 395.2049.

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-25be403787b54dccb9260bc109a8805c
Source dataset
uspto-grants-2006_11
Patent number
US07132437B2

Reaction notes

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