Hydrochloric Acid → HCID 86602696, compound

HRID 1375006Notes

Reaction equation

HRID 1375006 reaction equation
[F:1][C:2]([F:62])([F:61])[C:3]1[CH:4]=[C:5]([CH:54]=[C:55]([C:57]([F:60])([F:59])[F:58])[CH:56]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:16]=[N:17][N:18](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:19]=2)[CH2:10][C@H:9]1[CH2:39][C:40]1[CH:45]=[CH:44][C:43]([CH3:46])=[C:42]([O:47][CH2:48][O:49][CH2:50][CH2:51][O:52][CH3:53])[CH:41]=1)=[O:7].Cl.[OH-].[Na+].[Cl-].[Na+]>O1CCOCC1>[F:62][C:2]([F:1])([F:61])[C:3]1[CH:4]=[C:5]([CH:54]=[C:55]([C:57]([F:59])([F:58])[F:60])[CH:56]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:19]=[N:18][NH:17][CH:16]=2)[CH2:10][C@H:9]1[CH2:39][C:40]1[CH:45]=[CH:44][C:43]([CH3:46])=[C:42]([O:47][CH2:48][O:49][CH2:50][CH2:51][O:52][CH3:53])[CH:41]=1)=[O:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 86602697HCID 86602697, compound

Product 1

HCID 86602696HCID 86602696, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of (2R)-1-[3,5-bis(trifluoromethyl)-benzoyl]-2-[3-[(2-methoxyethoxy)methoxy]-4-methylbenzyl]-4-[(1-trityl-1H-pyrazol-4-yl)methyl]piperazine (1.184 g) in 1,4-dioxane (118 ml) was added 1N hydrochloric acid (71 ml) and the resulting mixture was stirred at 40° C. for 7 hours. After cooling, the pH of the mixture was adjusted to 7 with 4N sodium hydroxide solution and sodium chloride was added to the mixture. The organic layer was separated, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of methylene chloride and methanol (30:1) as eluent to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-[3-[(2-methoxyethoxy)methoxy]-4-methylbenzyl]-4-[(1H-pyrazol-4-yl)-methyl]piperazine (575 mg).

Workup

  1. temperatureAfter cooling
  2. additionwas added to the mixture
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel with a mixture of methylene chloride and methanol (30:1) as eluent

Sources & evidence

ORD record
ord-1030cc2952db4ff280184d1b6c52570c
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

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