Potassium Carbonate → HCID 19787719, compound

HRID 1656403Notes

Reaction equation

HRID 1656403 reaction equation
[C:1]1([C:11]2[N:12]=[C:13]([CH2:18][CH2:19][CH3:20])[NH:14][C:15]=2[CH:16]=[O:17])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Br[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[C:35]2[N:39]([C:40]([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[N:38]=[N:37][N:36]=2)=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:1]1([C:11]2[N:12]=[C:13]([CH2:18][CH2:19][CH3:20])[N:14]([CH2:22][C:23]3[CH:24]=[CH:25][C:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[C:35]4[N:39]([C:40]([C:53]5[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=5)([C:47]5[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=5)[C:41]5[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=5)[N:38]=[N:37][N:36]=4)=[CH:27][CH:28]=3)[C:15]=2[CH:16]=[O:17])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazoleHCID 54132950HCID 54132950, compound

Product 1

HCID 19787719HCID 19787719, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 4-(naphth-1-yl)-2-n-propylimidazole-5-carboxaldehyde (0.90 g, 39.7 mmol, 1 eq), 4-bromomethyl-2'-(N-triphenylmethyl-(1H-tetrazol-5-yl))biphenyl (2.03 g, 43.7 mmol), 1.1 eq), dry DMF (20 mL), and 3.0 g of potassium carbonate was stirred at room temperature for 18 h. The reaction mixture was filtered, the precipitate was washed with methylene chloride and evaporated under reduced pressure. The residue was chromatographed in 98:2 methylene chloride/ethyl acetate over silica gel to yield a yellow foam. Yield: 1.50 g. NMR (CDCl3) δ 9.45 (s, 1H); 7.85 (m, 1H); 6.86-7.45 (m, 29H); 5.55 (s, 2H); 2.60 (t, 2H); 1.80 (m, 2H); 0.95 (t, 3H). ##STR78##

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe precipitate was washed with methylene chloride
  3. customevaporated under reduced pressure
  4. customThe residue was chromatographed in 98:2 methylene chloride/ethyl acetate over silica gel
  5. customto yield a yellow foam

Sources & evidence

ORD record
ord-6f26334890f7489db38f5836cf9071fb
Source dataset
uspto-grants-1993_10
Patent number
US05254546

Reaction notes

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