1-Hydroxybenzotriazole → 4'-Isopropyl-5-methyl-biphenyl-2-carboxylic acid [4-[4-(3-cyano-benzyl)-piperazin-1-yl]-phenyl]-amide

HRID 1267124Notes

Reaction equation

HRID 1267124 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][CH:22]=1)[CH2:6][N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)#[N:2].[CH:23]([C:26]1[CH:31]=[CH:30][C:29]([C:32]2[C:33]([C:39](O)=[O:40])=[CH:34][CH:35]=[C:36]([CH3:38])[CH:37]=2)=[CH:28][CH:27]=1)([CH3:25])[CH3:24].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl.CCN(CC)CC>[C:1]([C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][CH:22]=1)[CH2:6][N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:39]([C:33]3[C:32]([C:29]4[CH:30]=[CH:31][C:26]([CH:23]([CH3:25])[CH3:24])=[CH:27][CH:28]=4)=[CH:37][C:36]([CH3:38])=[CH:35][CH:34]=3)=[O:40])=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)#[N:2]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 111854474-[4-(3-Cyano-benzyl)-piperazin-1-yl]-phenylamineHCID 185454504'-Isopropyl-5-methyl-biphenyl-2-carboxylic acid

Product 1

HCID 98716174'-Isopropyl-5-methyl-biphenyl-2-carboxylic acid [4-[4-(3-cyano-benzyl)-piperazin-1-yl]-phenyl]-amideYield 60.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a stirred solution of 4-[4-(3-cyano-benzyl)-piperazin-1-yl]-phenylamine (150 mg), 4′-isopropyl-5-methyl-biphenyl-2-carboxylic acid (127 mg), HOBt (87 mg), and Et3N (64 mg) in CH2Cl2 (10 mL) was added at room temperature EDCl (124 mg) and the mixture was stirred at room temperature for 16 hours. The organic solution was then washed with water, with a saturated solution of NaHCO3 and dried over Na2SO4. After filtration and evaporation of the filtrate, the oily residue was crystallized from EtOH to give the title compound (160 mg) as white crystals.

Workup

  1. washThe organic solution was then washed with water, with a saturated solution of NaHCO3
  2. dry with materialdried over Na2SO4
  3. filtrationAfter filtration and evaporation of the filtrate
  4. customthe oily residue was crystallized from EtOH

Sources & evidence

ORD record
ord-88efe41ae6b9428bb20a682655d1fac5
Source dataset
uspto-grants-2003_04
Patent number
US06552022B1

Reaction notes

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