Dimethylformamide → HCID 178440169, compound

HRID 248629Notes

Reaction equation

HRID 248629 reaction equation
C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[N:8]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]3[CH:24]=[CH:23][C:22]([CH2:25]Br)=[CH:21][CH:20]=3)=[N:11][N:10]=[N:9]2)C=CC=CC=1.[C:39]([C:41]1[NH:45][C:44]([CH2:46][CH2:47][CH3:48])=[N:43][C:42]=1[N:49]1[CH:53]=[CH:52][CH:51]=[C:50]1[C:54](=[O:59])[C:55]([F:58])([F:57])[F:56])#[N:40].CN(C)C=O.C([O-])([O-])=O.[K+].[K+]>C(OCC)(=O)C>[C:39]([C:41]1[N:45]([CH2:25][C:22]2[CH:23]=[CH:24][C:19]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[C:12]3[NH:8][N:9]=[N:10][N:11]=3)=[CH:20][CH:21]=2)[C:44]([CH2:46][CH2:47][CH3:48])=[N:43][C:42]=1[N:49]1[CH:53]=[CH:52][CH:51]=[C:50]1[C:54](=[O:59])[C:55]([F:58])([F:56])[F:57])#[N:40]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazoleHCID 14962885HCID 14962885, compound

Product 1

HCID 178440169HCID 178440169, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

N-triphenylmethyl 5-[4'-(bromomethyl)biphenyl-2yl]tetrazole (Example 26, 2.1 g), 5-cyano-4-[2-(1-oxo-2,2,2-trifluoroethyl)-1H-pyrrol-1-yl]-2-propylimidazole (Example 26, 0.89 g), N,N-dimethylformamide (10 mL), and anhydrous K2CO3 (0.5 g) were stirred at room temperature under nitrogen atmosphere for 24 hours. Ethyl acetate (50 mL) was added and inorganic solids were removed by filtration. The filtrate was evaporated at reduced pressure and the major product was isolated by flash chromatography on silica gel (toluene-acetonitrile 96:4) to afford the title compound in its triphenylmethyl protected form (1.3 g). This material was dissolved in methanol (50 mL), treated with aqueous 10% citric acid (1.5 mL) and heated at reflux for 90 minutes. After cooling to room temperature, water (10 mL) and hexanes (100 mL) were added and the mixture was shaken vigorously. The methanol layer was separated, washed again with hexanes and evaporated. The residue was partitioned between ethyl acetate and water. The ethyl acetate layer was dried over anhydrous magnesium sulfate and evaporated. The resulting gum was dissolved in ether, concentrated and allowed to stand overnight to give some seed crystals. The remaining gum was dissolved in tertbutyl methyl ether, seeded and diluted with diisopropyl ether. Crystallization gave the title product after filtration. MS (CI, CH4 +NH3) 531 (m+1).

Workup

  1. custominorganic solids were removed by filtration
  2. customThe filtrate was evaporated at reduced pressure
  3. customthe major product was isolated by flash chromatography on silica gel (toluene-acetonitrile 96:4)

Sources & evidence

ORD record
ord-eafce0eb66c64499a44c8b4f01091871
Source dataset
uspto-grants-1993_05
Patent number
US05210211

Reaction notes

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