Hydrochloric Acid → HCID 57931283, compound

HRID 2261862Notes

Reaction equation

HRID 2261862 reaction equation
C[O:2][C:3](=[O:44])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11](C(OC(C)(C)C)=O)[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]3[N:21]([C:28]4[C:33]([Cl:34])=[CH:32][CH:31]=[CH:30][C:29]=4[Cl:35])[N:22]=[CH:23][C:24]=3[CH:25]([CH3:27])[CH3:26])=[CH:14][C:13]=2[CH3:36])[CH:5]=1.Cl>O1CCOCC1>[Cl:35][C:29]1[CH:30]=[CH:31][CH:32]=[C:33]([Cl:34])[C:28]=1[N:21]1[C:20]([CH2:19][O:18][C:15]2[CH:16]=[CH:17][C:12]([NH:11][CH2:10][C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([OH:44])=[O:2])=[C:13]([CH3:36])[CH:14]=2)=[C:24]([CH:25]([CH3:27])[CH3:26])[CH:23]=[N:22]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67528061HCID 67528061, compound

Product 1

HCID 57931283HCID 57931283, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a 0° C. solution of 3-[(tert-Butoxycarbonyl-{4-[2-(2,6-dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-amino)-methyl]-benzoic acid methyl ester (797 mg, 1.24 mmol) in dioxane (10 mL) is added hydrochloric acid (3.12 mL, 12.40 mmol, 4M in dioxane) dropwise. The reaction is warmed to room temperature and is stirred overnight. The reaction mixture is concentrated under reduced pressure and the residue is partitioned between EtOAc and saturated aqueous NaHCO3. The aqueous layer is extracted with EtOAc and the combined organic layers are washed with brine, dried (MgSO4), filtered, and concentrated under reduced pressure. The residue is chromatographed (SiO2 120 g, 0% to 30% EtOAc/Hex) to yield the title compound (603 mg, 90%). ES/MS m/e (35Cl) 524.0 (M+1)

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customthe residue is partitioned between EtOAc and saturated aqueous NaHCO3
  3. extractionThe aqueous layer is extracted with EtOAc
  4. washthe combined organic layers are washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is chromatographed (SiO2 120 g, 0% to 30% EtOAc/Hex)

Sources & evidence

ORD record
ord-76067b0fade1486fbe1f70f5042e6399
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

Loading…