Hydrochloric Acid → HCID 178441680, compound

HRID 274138Notes

Reaction equation

HRID 274138 reaction equation
[Br:1][C:2]1[N:3]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]2[N:31]=[N:32][N:33](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:34]=2)[N:4]=[C:5]2[C:10]=1[CH:9]=[C:8]([CH2:11][N:12]1[C:16]([CH:17]=[O:18])=[C:15]([Cl:19])[N:14]=[C:13]1[CH2:20][CH2:21][CH2:22][CH3:23])[CH:7]=[CH:6]2.Cl.[OH-].[Na+]>CO>[Br:1][C:2]1[N:3]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]2[NH:34][N:33]=[N:32][N:31]=2)[N:4]=[C:5]2[C:10]=1[CH:9]=[C:8]([CH2:11][N:12]1[C:16]([CH:17]=[O:18])=[C:15]([Cl:19])[N:14]=[C:13]1[CH2:20][CH2:21][CH2:22][CH3:23])[CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 313Hydrochloric Acid3×HCID 14798Sodium HydroxideHCID 20094519HCID 20094519, compound

Product 1

HCID 178441680HCID 178441680, compoundYield 32.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
10 °C

Procedure

Methanol (2 ml) was added to 1-{[3-bromo-2-[2-(2-(triphenylmethyl)-2H-tetrazol-5-yl)phenyl]-2H-indazol-5-yl]methyl}-2-butyl-4-chloro-1H-imidazole-5-carbaldehyde (0.200 g, 0.256 mmol) as obtained in Example 11, and the mixture was stirred at 10°C. Thereto was added 2N hydrochloric acid (0.23 ml), and the mixture was stirred at room temperature for 2 hours. Then, 2N hydrochloric acid (0.23 ml) and methanol (2.5 ml) were added thereto, and the mixture was stirred for 3 hours, after which conc. hydrochloric acid (2 ml) was added thereto and the mixture was stirred for 15.5 hours. 10N Aqueous sodium hydroxide was added to adjust its pH to 13, and the methanol was distilled away in an evaporator. The resultant solid was filtered, and the cake was washed twice with 1N sodium hydroxide (2.5 ml). The filtrate was washed with ether (5 ml), and conc. hydrochloric acid was dropwise added while stirring so as to adjust its pH to 4-5. The resultant solid was filtered off and washed twice with ion-exchanged water (5 ml). Drying in vacuo at 37° C. gave 45 mg of 1-{[3-bromo-2-[2-(1H-tetrazol-5-yl)phenyl]-2H-indazol-5-yl]methyl}-2-butyl-4-chloro-1H-imidazole-5-carbaldehyde.

Workup

  1. customas obtained in Example 11
  2. stirringthe mixture was stirred at room temperature for 2 hours
  3. stirringthe mixture was stirred for 3 hours
  4. stirringthe mixture was stirred for 15.5 hours
  5. distillationthe methanol was distilled away in an evaporator
  6. filtrationThe resultant solid was filtered
  7. washthe cake was washed twice with 1N sodium hydroxide (2.5 ml)
  8. washThe filtrate was washed with ether (5 ml), and conc. hydrochloric acid
  9. additionwas dropwise added
  10. stirringwhile stirring so as
  11. filtrationThe resultant solid was filtered off
  12. washwashed twice with ion-exchanged water (5 ml)
  13. customDrying in vacuo at 37° C.

Sources & evidence

ORD record
ord-457c209dddab44c6b4c994ab51fd9cdb
Source dataset
uspto-grants-1995_02
Patent number
US05387684

Reaction notes

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