Hydrochloric Acid → HCID 178440176, compound

HRID 248632Notes

Reaction equation

HRID 248632 reaction equation
[O:1]=[C:2]([C:7]1[N:8]([C:12]2[N:13]=[C:14]([CH2:39][CH2:40][CH3:41])[N:15]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[C:34]4[NH:38][N:37]=[N:36][N:35]=4)=[CH:24][CH:23]=3)[C:16]=2[C:17]([O:19]C)=[O:18])[CH:9]=[CH:10][CH:11]=1)C(F)(F)F.Cl.[OH-:43].[Na+]>O>[C:17]([C:16]1[N:15]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]3[NH:35][N:36]=[N:37][N:38]=3)=[CH:26][CH:27]=2)[C:14]([CH2:39][CH2:40][CH3:41])=[N:13][C:12]=1[N:8]1[CH:9]=[CH:10][CH:11]=[C:7]1[C:2]([OH:43])=[O:1])([OH:19])=[O:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178440171HCID 178440171, compound

Product 1

HCID 178440176HCID 178440176, compoundYield 120.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 4-[2-(1-oxo-2,2,2-trifluoroethyl)-1H-pyrrol-1-yl]-2-propyl-1-[(2'-(1H-tetrazol-5-yl)biphen-4-yl)methyl]-1H-imidazole-5-carboxylate (Example 13, 0.8 g) was dissolved in a solution sodium hydroxide (1.68 g) in water (14 mL) and the resulting solution refluxed overnight. After cooling in an ice bath, conc HCl was added dropwise until the pH of the mixture was between 3-4. The insoluble product was collected by filtration, washed several times with water, and dried under reduced pressure overnight at room temperature to afford 0.85 g of the title compound 1H-NMR (DMSO-d6) δ 7.8 7.5 (m, 4H), 7.3-7.0 (m, 5H), 6.9 (m, H), 6.3 (m, 1H), 5.7 (s, 2H), 2.6 (t, 2H), 1.7 1.4 (m, 2H), 0.9 (t, 3H).

Workup

  1. temperaturethe resulting solution refluxed overnight
  2. temperatureAfter cooling in an ice bath
  3. filtrationThe insoluble product was collected by filtration
  4. washwashed several times with water
  5. customdried under reduced pressure overnight at room temperature

Sources & evidence

ORD record
ord-e60be3905efe41a1816b20eac454e68d
Source dataset
uspto-grants-1993_05
Patent number
US05210211

Reaction notes

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