Ammonium Hydroxide → HCID 77779172, compound

HRID 1934580Notes

Reaction equation

HRID 1934580 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)[CH3:27])[C:21]4=[O:30])=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:31][C@@H:32]([C:34]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]=[CH:36][CH:35]=1)[NH2:33].[Na].[NH4+].[OH-]>C(Cl)Cl>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:15]=[CH:16][C:17]([N:20]4[CH:24]=[N:23][N:22]([CH:25]([CH3:29])[CH:26]([NH:33][CH:32]([C:34]5[C:43]6[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=6)[CH:37]=[CH:36][CH:35]=5)[CH3:31])[CH3:27])[C:21]4=[O:30])=[CH:18][CH:19]=3)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 14923Ammonium HydroxideHCID 663251-Naphthalenemethanamine, alpha-methyl-, (alphaS)-HCID 5360545SodiumHCID 151255654-[4-[4-(4-Hydroxyphenyl)piperazin-1-yl]phenyl]-2-(3-oxobutan-2-yl)-1,2,4-triazol-3-one

Product 1

HCID 77779172HCID 77779172, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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 (0.018 mol), (S)-α-methyl-1-naphthalenemethanamine (0.0187 mol) and sodium tris(acetato-O)hydroborate (I-) (0.028 mol) in CH2Cl2 (150 ml) was stirred at room temperature overnight. A diluted NH4OH solution was added. The mixture was stirred for 1 hour. The precipitate was filtered off, washed with H2O and with CH2Cl2 (20 ml) and dried. The residue was crystallized from CH3CN. The precipitate was filtered off and dried, yielding 3.3 g (32%) of [R-(R*,S*)(S*)]-2,4-dihydro-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-2-[1-metyl-2-[[1-(1-naphthalenyl)ethyl]amino]propyl]-3H-1,2,4-triazol-3-one (interm. 108).

Workup

  1. stirringThe mixture was stirred for 1 hour
  2. filtrationThe precipitate was filtered off
  3. washwashed with H2O and with CH2Cl2 (20 ml)
  4. customdried
  5. customThe residue was crystallized from CH3CN
  6. filtrationThe precipitate was filtered off
  7. customdried

Sources & evidence

ORD record
ord-bf9646e6b1374abb9301287fb82580cd
Source dataset
uspto-grants-2002_05
Patent number
US06384030B1

Reaction notes

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