Hydrochloric Acid → HCID 178441681, compound

HRID 274139Notes

Reaction equation

HRID 274139 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]([CH2:17][OH:18])=[C:15]([Cl:19])[N:14]=[C:13]1[CH2:20][CH2:21][CH2:22][CH3:23])[CH:7]=[CH:6]2.Cl>ClCCl.C(O)C>[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]([CH2:17][OH: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 2

HCID 313Hydrochloric AcidHCID 20094539HCID 20094539, compound

Product 1

HCID 178441681HCID 178441681, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To 1-{[3-bromo-2-[2-(2-(triphenylmethyl)-2H-tetrazol-5-yl)phenyl]-2H-indazol-5-yl]methyl}-2-butyl-4-chloro-5-(hydroxymethyl)-1H-imidazole (obtained in Example 13) in dichloromethane (8.4 ml ) was dropwise added 14.7% hydrogen chloride in ethanol (5.6 ml), and the mixture was stirred at room temperature for 17 hours. The mixture was concentrated in an evaporator, and thereto were added water (5 ml), 10N aqueous sodium hydroxide (1.25 ml), and 1N aqueous sodium hydroxide (5 ml), followed by filtration. The cake was washed twice with water (5 ml), and conc. hydrochloric acid was dropwise added to the filtrate while stirring so as to adjust its pH to 4-5. The resultant solid was filtered off, washed twice with ion-exchanged water (2 ml), and dried in vacuo at 37° C. to give 11 mg of 1-{[3-bromo-2-[2-(1H-tetrazol-5-yl)phenyl]-2H-indazol- 5-yl]methyl}-2-butyl-4-chloro-5-(hydroxymethyl)-1H-imidazole.

Workup

  1. concentrationThe mixture was concentrated in an evaporator
  2. additionwere added water (5 ml), 10N aqueous sodium hydroxide (1.25 ml), and 1N aqueous sodium hydroxide (5 ml)
  3. filtrationfollowed by filtration
  4. washThe cake was washed twice with water (5 ml), and conc. hydrochloric acid
  5. additionwas dropwise added to the filtrate
  6. stirringwhile stirring so as
  7. filtrationThe resultant solid was filtered off
  8. washwashed twice with ion-exchanged water (2 ml)
  9. customdried in vacuo at 37° C.

Sources & evidence

ORD record
ord-a2babc7759874bcf974daea3fdcfd281
Source dataset
uspto-grants-1995_02
Patent number
US05387684

Reaction notes

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