5-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazole → HCID 178440167, compound
Reaction equation
[C:1]([C:3]1[NH:7][C:6]([CH2:8][CH2:9][CH3:10])=[N:5][C:4]=1[N:11]1[CH:15]=[CH:14][CH:13]=[CH:12]1)#[N:2].CC(C)([O-])C.[K+].C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[N:29]2[C:33]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[C:40]3[CH:45]=[CH:44][C:43]([CH2:46]Br)=[CH:42][CH:41]=3)=[N:32][N:31]=[N:30]2)C=CC=CC=1>>[C:1]([C:3]1[N:7]([CH2:46][C:43]2[CH:44]=[CH:45][C:40]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=3[C:33]3[NH:29][N:30]=[N:31][N:32]=3)=[CH:41][CH:42]=2)[C:6]([CH2:8][CH2:9][CH3:10])=[N:5][C:4]=1[N:11]1[CH:12]=[CH:13][CH:14]=[CH:15]1)#[N:2]Participants
Procedure
Using the method described in Example 15, 5-cyano 2 propyl-4-(1H-pyrrol-1-yl)imidazole (Example 19, 2.0 g), potassium tert butoxide (1.2 g) and N-triphenylmethyl-5-[4'-(bromomethyl)biphenyl-2yl]tetrazole (Example 12, 7.0 g) were reacted to give the title product in its triphenylmethyl protected form after purification by chromatography. This material was dissolved in methanol (200 mL), treated with aqueous 10% citric acid (10 mL) and heated at reflux for 2.5 hours. The resulting solution was diluted with water (40 mL) and washed twice with hexanes. The methanol-water layer was evaporated and the residue was partitioned between ethyl acetate and water. The organic layer was dried over anhydrous magnesium sulfate and evaporated to a gum. This gum was dissolved in tert-butyl methyl ether and evaporated to a gum which was allowed to stand until seed crystals formed. Trituration with tert-butyl methyl ether gives the title compound as a crystalline solid, mp 179°-181° C. MS (CI, CH4 +NH3) 435 (m+1).
Workup
- customwere reacted
Sources & evidence
- ORD record
- ord-6a934d8ee1684bfeaefcd2e76c05ee54
- Source dataset
- uspto-grants-1993_05
- Patent number
- US05210211
Reaction notes
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