Ammonium Chloride → HCID 15125573, compound

HRID 1934582Notes

Reaction equation

HRID 1934582 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][C:17]([N:20]4[CH:24]=[N:23][N:22]([CH:25]([CH3:29])[C:26](=[O:28])[CH3:27])[C:21]4=[O:30])=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C([BH-](C(CC)C)C(CC)C)(CC)C.[K+].[NH4+].[Cl-]>CN(C=O)C.C1COCC1>[OH:28][CH:26]([CH3:27])[CH:25]([N:22]1[C:21](=[O:30])[N:20]([C:17]2[CH:16]=[CH:15][C:14]([N:11]3[CH2:10][CH2:9][N:8]([C:5]4[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=4)[CH2:13][CH2:12]3)=[CH:19][CH:18]=2)[CH:24]=[N:23]1)[CH3:29]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4304157Potassium;tri(butan-2-yl)boranuideHCID 151255654-[4-[4-(4-Hydroxyphenyl)piperazin-1-yl]phenyl]-2-(3-oxobutan-2-yl)-1,2,4-triazol-3-one

Product 1

HCID 15125573HCID 15125573, compoundYield 0.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (±)-2,4-dihydro-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-2-(1-methyl-2-oxopropyl)-3H-1,2,4-triazol-3-one (0.120 mol) in DMF (700 ml) was cooled on ice. Potassium tri-sec-butylborohydride, 1M solution in THF (300 ml) was added dropwise. The mixture was allowed to warm to room temperature, then poured out into an aqueous NH4Cl solution. The precipitate was filtered off, dried and crystallized from 2-propanol. This fraction was separated into its enantiomers over CHIRALPAC AD [(amylose 3,5 dimethylphenyl carbamate) purchased from Daicel Chemical Industries, Ltd, in Japan] (eluent: 100% ethanol). Two pure fraction groups were collected and their solvent was evaporated. The desired fraction was recrystallized from methanol. The precipitate was filtered off and dried, yielding 0.9 g of [R-(R*,R*)]-2,4-dihydro-2-(2-hydroxy-1methylpropyl)-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-3H-1,2,4-triazol-3-one (interm. 14a; [α]20D=+10.35° @ 48.61 mg/5 ml in DMF) and 0.8 g [S-(R*,R*)]-2,4-dihydro-2-(2-hydroxy-1-methylpropyl)-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-3H-1,2,4-triazol-3-one (interm. 14b).

Workup

  1. temperaturewas cooled on ice
  2. filtrationThe precipitate was filtered off
  3. customdried
  4. customcrystallized from 2-propanol
  5. customThis fraction was separated into its enantiomers over CHIRALPAC AD [(amylose 3,5 dimethylphenyl carbamate) purchased from Daicel Chemical Industries, Ltd, in Japan] (eluent: 100% ethanol)
  6. customTwo pure fraction groups were collected
  7. customtheir solvent was evaporated
  8. customThe desired fraction was recrystallized from methanol
  9. filtrationThe precipitate was filtered off
  10. customdried

Sources & evidence

ORD record
ord-7c40d0d720644220a22216bebcd80254
Source dataset
uspto-grants-2002_05
Patent number
US06384030B1

Reaction notes

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