HCID 15698061, compound → HCID 178441674, compound

HRID 847063Notes

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[C:27]([OH:29])=O)=[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].[NH2:30][C:31]1[NH:35][N:34]=[N:33][N:32]=1>>[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[C:27]([NH:30][C:31]3[NH:35][N:34]=[N:33][N:32]=3)=[O: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]

Participants

Reactant 2

HCID 15698061HCID 15698061, compound

HCID 178509299HCID 178509299, compound

Product 1

HCID 178441674HCID 178441674, compound

Procedure

2-n-Butyl-1-[(2'-carboxybiphenyl-4-yl)methyl]-4-chloro-5-(methoxymethyl)imidazole (1.0 g) was first converted to the corresponding acid chloride and then coupled to 5-aminotetrazole by the procedure in Example 78, Part C to yield 0.87 g of a yellow glass. Flash chromatography in 100% ethyl acetate over silica gel yielded 77.1 mg of a white solid; m.p. 169°-173°. NMR (200 MHz, CDCl3, DMSO-d6)δ12.0 (br s, 1H); 7.73-7.30 (m, 6H); 7.00 (d, 2H, J=7 Hz); 5.18 (s, 2H); 4.23 (s, 2H); 2.55 (t, 2H, J=7 Hz) 1.63 (t of t, 2H, J=7,7 Hz); 1.31 (t of q, 2H, J=7,7 Hz); 0.84 (t, 3H, J=7 Hz). Anal. Calcd. for C24H26ClN7O2 · (H2O)2 : C, 55.87; H, 5.86. Found: C, 56.01; H, 6.01.

Sources & evidence

ORD record: ord-47e012b1fe2e4ee8b8dbbdd72fc79624
Source dataset: uspto-grants-1992_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05138069

Reaction notes

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