Hydrochloric Acid → [2-Chloro-4-(4-fluoro-phenylamino)-phenyl]-{5-[1-(2,3-dihydroxy-propyl)-1H-[1,2,3]triazol-4-yl]-2-methyl-phenyl}-methanone

HRID 2067231Notes

Reaction equation

HRID 2067231 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:16]([C:18]1[CH:23]=[C:22]([C:24]2[N:25]=[N:26][N:27]([CH2:29][CH:30]3[CH2:34][O:33]C(C)(C)[O:31]3)[CH:28]=2)[CH:21]=[CH:20][C:19]=1[CH3:37])=[O:17].Cl.CCOC(C)=O.O.C([O-])(O)=O.[Na+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([F:15])=[CH:13][CH:14]=2)[CH:5]=[CH:4][C:3]=1[C:16]([C:18]1[CH:23]=[C:22]([C:24]2[N:25]=[N:26][N:27]([CH2:29][CH:30]([OH:31])[CH2:34][OH:33])[CH:28]=2)[CH:21]=[CH:20][C:19]=1[CH3:37])=[O:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11685044HCID 11685044, compoundHCID 23687555EtOAc water NaHCO3

Product 1

HCID 11705693[2-Chloro-4-(4-fluoro-phenylamino)-phenyl]-{5-[1-(2,3-dihydroxy-propyl)-1H-[1,2,3]triazol-4-yl]-2-methyl-phenyl}-methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of compound 123 (1.05 g, 2.02 mmol) in THF (10 mL) was added HCl (10 mL, aq., 10, 1N) and the mixture was stirred for 16 h at RT. The reaction mixture was poured into a mixture of EtOAc/water/NaHCO3. The organic phase was washed with water, brine and then dried (MgSO4), filtered and concentrated in vacuo to give the crude product. The crude product was purified by continuous gradient flash chromatography using MeOH/DCM 0:100 to 10:90 as the eluent to afford the title compound as white solid.

Workup

  1. washThe organic phase was washed with water, brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give the crude product
  6. customThe crude product was purified by continuous gradient flash chromatography

Sources & evidence

ORD record
ord-8f208705efa74cb4a809faca34b0ea7c
Source dataset
uspto-grants-2012_10
Patent number
US08293772B2

Reaction notes

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