Hydrochloric Acid → HCID 178440107, compound

HRID 258112Notes

Reaction equation

HRID 258112 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([CH2:28][CH2:29][CH3:30])[N:5]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[NH:27][N:26]=[N:25][N:24]=3)=[CH:13][CH:12]=2)[C:6]=1[C:7](O)=[O:8].C(C1NC=CN=1)(C1NC=CN=1)=O.[NH2:43][CH2:44][CH2:45][C:46]1[CH:51]=[CH:50][C:49]([OH:52])=[CH:48][CH:47]=1.Cl>O1CCCC1.O.CC(O)C>[Cl:1][C:2]1[N:3]=[C:4]([CH2:28][CH2:29][CH3:30])[N:5]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[NH:24][N:25]=[N:26][N:27]=3)=[CH:13][CH:12]=2)[C:6]=1[C:7]([NH:43][CH2:44][CH2:45][C:46]1[CH:51]=[CH:50][C:49]([OH:52])=[CH:48][CH:47]=1)=[O:8]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 5610TyramineHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 178440110HCID 178440110, compound

Product 1

HCID 178440107HCID 178440107, compoundYield 50.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 4.86 g of 4-chloro-2-propyl-1-[[2'-(tetrazol-5-yl)biphenyl-4-yl]methyl]imidazole-5-carboxylic acid in 115 mL of tetrahydrofuran at 25° C. is added 2.25 g of carbonyl diimidazole, and the resulting solution is stirred at 25° C. for 3 hours. To the solution is added 3.94 g of tyramine and 23 mL of 2-propanol, and the mixture was stirred at 25° C. for an additional 3 hours. The reaction mixture is poured into water, and the resulting emulsion is adjusted to pH 3 employing hydrochloric acid and then extracted with chloroform. The combined extracts are washed with water and brine, dried over anhydrous sodium sulfate, and concentrated. Column chromatography (elution: 10% 2- propanol/chloroform) affords 3.15 g of the product as an amorphous solid. NMR (300 MHz, DMSO-d6) δ 8.07 (t, 1H, J=8 Hz), 7.69-7.50 (m, 4H), 7.07-6.99 (m, 6H), 6.65 (d, 2H, J=8 Hz), 5.42 (s, 2H), 3.36 (quart., 2H, J=7 Hz), 2.63 (t, 2H, J=7 Hz), 2.50 (t, 2H, J=7 Hz), 1.51 (sext., 2H, J=7 Hz), 0.82 (t, 3H, J=7 Hz).

Workup

  1. stirringthe mixture was stirred at 25° C. for an additional 3 hours
  2. extractionextracted with chloroform
  3. washThe combined extracts are washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. washColumn chromatography (elution: 10% 2- propanol/chloroform)

Sources & evidence

ORD record
ord-0eeb67d7df894f4fa38c8cfb9e832969
Source dataset
uspto-grants-1993_11
Patent number
US05264581

Reaction notes

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