HCID 15698101, compound → HCID 178441673, compound

HRID 847064Notes

Reaction equation

HRID 847064 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH2:27][C:28]#[N:29])=[CH:17][CH:16]=2)[C:7]([CH2:11][O:12][CH3:13])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4].[NH:30]1C=N[N:32]=[N:31]1.CCCCCC.C(OCC)(=O)C>C(OCC)(=O)C.C(O)(C)C>[CH2:1]([C:5]1[N:6]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH2:27][C:28]3[NH:32][N:31]=[N:30][N:29]=3)=[CH:19][CH:20]=2)[C:7]([CH2:11][O:12][CH3:13])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 15698101HCID 15698101, compoundHCID 21226206Ethyl acetate hexaneHCID 178418441HCID 178418441, compound

Product 1

HCID 178441673HCID 178441673, compound

Reagents, catalysts & solvents 1

HCID 22055037Isopropanol ethyl acetateSolvent

Procedure

2-n-Butyl-4-chloro-1-[(2'-(cyanomethyl)biphenyl-4-yl)methyl]-5-(methoxymethyl)imidazole (5.20 g) was converted to the above tetrazole in 2 days using the procedure of Example 90, Part C. Work-up and flash chromatography over silica gel eluting with a gradient solvent system of 1:1 hexane/ethyl acetate to 1:1 ethyl acetate/isopropanol yielded 3.13 g of a light yellow solid; m.p. 149.0°-152.5°. NMR (200 MHz, CDCl3)δ7.37-7.15 (m, 6H); 6.96 (d, 2H, J=9 Hz); 5.18 (s, 2H); 4.30 (s, 2H); 4.24 (s, 2H); 3.27 (s, 3H); 2.57 (t, 2H, J=7 Hz); 1.56 (t of t, 2H, J=7,7 Hz); 1.28 (t of q, 2H, J=7,7 Hz); 0.77 (t, 3H, J=7 Hz). Anal. Calcd. for C24H27ClN 6 O: C, 63.97, H, 6.03; Cl, 7.86. Found: C, 63.79; H, 6.04; Cl, 7.70.

Sources & evidence

ORD record
ord-8caa356664704e9c96c81d3ab33c1ab1
Source dataset
uspto-grants-1992_08
Patent number
US05138069

Reaction notes

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