Hydrochloric Acid → HCID 58243859, compound

HRID 389137Notes

Reaction equation

HRID 389137 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][C:20]([CH3:38])([C:22]2[N:26]([CH3:27])[C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]([F:37])([F:36])[F:35])=[N:24][N:23]=2)[CH3:21])=[C:6]([CH:18]=1)[C:7]([NH:9][CH2:10][CH:11]1[CH2:15][O:14]C(C)(C)[O:12]1)=[O:8].Cl.O>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][C:20]([CH3:38])([C:22]2[N:26]([CH3:27])[C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]([F:36])([F:37])[F:35])=[N:24][N:23]=2)[CH3:21])=[C:6]([CH:18]=1)[C:7]([NH:9][CH2:10][CH:11]([OH:12])[CH2:15][OH:14])=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 962WaterHCID 67024390HCID 67024390, compound

Product 1

HCID 58243859HCID 58243859, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-chloro-N-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-2-(1-methyl-1-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}ethoxy)benzamide (362 mg) was suspended in THF (10 ml), 1M hydrochloric acid (10 ml) was added thereto, followed by stirring at room temperature for 2 hours, warming to 50° C. and stirring for 30 minutes. The reaction solution was cooled to room temperature, and water and 1M hydrochloric acid were added thereto, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and concentrated under reduced pressure. The resulting solid was washed with diisopropylether to obtain, as a white solid, 5-chloro-N-(2,3-dihydroxypropyl)-2-(1-methyl-1-{4-methyl-5-[2-(trifluoromethyl)phenyl)-4H-1,2,4-triazol-3-yl}ethoxy)benzamide (293 mg).

Workup

  1. temperaturewarming to 50° C.
  2. stirringstirring for 30 minutes
  3. temperatureThe reaction solution was cooled to room temperature
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. concentrationconcentrated under reduced pressure
  7. washThe resulting solid was washed with diisopropylether

Sources & evidence

ORD record
ord-c2144e85465b4a92969ad2227aae8b29
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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