4-Methylmorpholine → 5(S)-Butyl-4-[1-(4-cyanobenzyl)-2-methyl-5-imidazolylmethyl]-1-(2,3-dimethylphenyl)piperazin-2-one dihydrochloride

HRID 342153Notes

Reaction equation

HRID 342153 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:15]([C:17]1[CH:31]=[CH:30][C:20]([CH2:21][N:22]2[C:26]([CH:27]=O)=[CH:25][N:24]=[C:23]2[CH3:29])=[CH:19][CH:18]=1)#[N:16].[ClH:32].[CH2:33]([C@H:37]1[CH2:42][N:41]([C:43]2[CH:48]=[CH:47][CH:46]=[C:45]([CH3:49])[C:44]=2[CH3:50])[C:40](=[O:51])[CH2:39][NH:38]1)[CH2:34][CH2:35][CH3:36].CN1CCOCC1.C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>ClC(Cl)C>[ClH:32].[ClH:32].[CH2:33]([C@H:37]1[CH2:42][N:41]([C:43]2[CH:48]=[CH:47][CH:46]=[C:45]([CH3:49])[C:44]=2[CH3:50])[C:40](=[O:51])[CH2:39][N:38]1[CH2:27][C:26]1[N:22]([CH2:21][C:20]2[CH:30]=[CH:31][C:17]([C:15]#[N:16])=[CH:18][CH:19]=2)[C:23]([CH3:29])=[N:24][CH:25]=1)[CH2:34][CH2:35][CH3:36]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 153910091-(4-Cyanobenzyl)-2-methylimidazole-5-carboxaldehydeHCID 229410585(S)-butyl-1-(2,3-dimethylphenyl)piperazin-2-one hydrochloride

Product 1

HCID 676334315(S)-Butyl-4-[1-(4-cyanobenzyl)-2-methyl-5-imidazolylmethyl]-1-(2,3-dimethylphenyl)piperazin-2-one dihydrochloride

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Sodium triacetoxyborohydride (0.265 g, 1.25 mmol) was added to a solution of 1-(4-cyanobenzyl)-2-methylimidazole-5-carboxaldehyde (0.190 g, 0.843 mmol), 5(S)-butyl-1-(2,3-dimethylphenyl)piperazin-2-one hydrochloride (0.250 g, 0.843 mmol), N-methylmorpholine (0.093 mL, 0.843 mmol) in dichloroethane (10 mL), according to the procedure described in Example 39, Step E. The title compound was purified by preparative HPLC using a gradient of 70 to 45% Solvent A. The free base was isolated and converted to dihydrochloride salt. The title compound was obtained as a white solid. FAB ms: 470 (M+1). Anal. Calc for C29H35N5O.2 HCl.1.45 H2O, C, 61.25; H, 7.07; N, 12.32. Found: C, 61.56; H, 6.99; N, 11.32.

Workup

  1. customThe title compound was purified by preparative HPLC
  2. customThe free base was isolated

Sources & evidence

ORD record
ord-7f506120326545c981fbc245461f3bcc
Source dataset
uspto-grants-1999_01
Patent number
US05856326

Reaction notes

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