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Sodium Methoxide → 1-[(2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1H-1, 2,4-triazol-1-yl)-2-butylsulfonyl]-4-(4-methyl-4H-1,2,4-triazol-3-ylmethyl) piperazine

HRID 274607
Notes
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Reaction equation

HRID 274607 reaction equation
Cl.Cl.[F:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[C@@:11]([OH:29])([CH2:23][N:24]1[CH:28]=[N:27][CH:26]=[N:25]1)[C@H:12]([S:14]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)(=[O:16])=[O:15])[CH3:13].Cl.Cl[CH2:32][C:33]1[N:37]([CH3:38])[CH:36]=[N:35][N:34]=1.C[O-].[Na+]>CO>[F:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[C@@:11]([OH:29])([CH2:23][N:24]1[CH:28]=[N:27][CH:26]=[N:25]1)[C@H:12]([S:14]([N:17]1[CH2:22][CH2:21][N:20]([CH2:32][C:33]2[N:37]([CH3:38])[CH:36]=[N:35][N:34]=2)[CH2:19][CH2:18]1)(=[O:16])=[O:15])[CH3:13]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 186592571-[(2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)-2-butylsulfonyl]piperazine.dihydrochloride2×HCID 223819093-(chloromethyl)-4-methyl-4H-1,2,4-triazole hydrochloride

Product 1

HCID 542808911-[(2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1H-1, 2,4-triazol-1-yl)-2-butylsulfonyl]-4-(4-methyl-4H-1,2,4-triazol-3-ylmethyl) piperazineYield 25.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
70 °C

Procedure

In methanol (6 ml) were dissolved 1-[(2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)-2-butylsulfonyl]piperazine-dihydrochloride (Compound 20, 0.40 g) and 3-chloromethyl-4-methyl-4H1,2,4-triazole.hydrochloride (255 mg). To the solution was added 1N-methanol solution of sodium methylate (3.69 ml), and the mixture was heated at 70° C. for 14 hours, then the reaction mixture was concentrated. The concentrate was dissolved in dichloromethane (30 ml), washed with water, dried and concentrated. The concentrate was recrystallized from ethyl acetate to give 1-[(2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1H-1, 2,4-triazol-1-yl)-2-butylsulfonyl]-4-(4-methyl-4H-1,2,4-triazol-3-ylmethyl) piperazine (Compound 26, 108 mg) as pale yellow crystals.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. dissolutionThe concentrate was dissolved in dichloromethane (30 ml)
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe concentrate was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a59c09cb34ee419c8919fb697eaf4bb6
Source dataset
uspto-grants-1995_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05389663

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes