Water → HCID 15125573, compound

HRID 48477Notes

Reaction equation

HRID 48477 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+].O>CN(C=O)C.O1CCCC1>[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 962WaterHCID 4304157Potassium;tri(butan-2-yl)boranuideHCID 151255654-{4-[4-(4-Hydroxyphenyl)piperazin-1-yl]phenyl}-2-(3-oxobutan-2-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 15125573HCID 15125573, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

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 (0.06 mol) in DMF (500 ml) was cooled to −10° C. and then stirred under N2 flow. Potassium tri-sec-butylborohydride, 1M solution in tetrahydrofuran (150 ml) was added dropwise. The mixture was allowed to warm to room temperature slowly and then poured out into water. The precipitate was filtered off, washed with CH3OH and crystallized from CH3OH. The precipitate was filtered off and dried. The residue was purified by HPLC over CHIRALPAC AD (eluent: ethanol). Two pure fractions were collected and their solvents were evaporated. Each residue was triturated in CH3OH. The precipitate was filtered off and dried, yielding 7.3 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. 1a) [α]20D=−10.81° (c=50.43 mg/5 ml DMF).

Workup

  1. temperatureto warm to room temperature slowly
  2. filtrationThe precipitate was filtered off
  3. washwashed with CH3OH
  4. customcrystallized from CH3OH
  5. filtrationThe precipitate was filtered off
  6. customdried
  7. customThe residue was purified by HPLC over CHIRALPAC AD (eluent: ethanol)
  8. customTwo pure fractions were collected
  9. customtheir solvents were evaporated
  10. customEach residue was triturated in CH3OH
  11. filtrationThe precipitate was filtered off
  12. customdried

Sources & evidence

ORD record
ord-06a969b7c3924dfc9cf150d91d039ab1
Source dataset
uspto-grants-2004_03
Patent number
US06703506B2

Reaction notes

Loading…