Diisopropylethylamine → HCID 44386230, compound

HRID 343716Notes

Reaction equation

HRID 343716 reaction equation
[ClH:1].[C:2]1([C:8]2([C:14]([NH2:16])=[O:15])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:17][C:18]1[CH:19]=[C:20]([CH:24]=[C:25]([Br:29])[C:26]=1[O:27][CH3:28])[C:21]([OH:23])=O.C([N:33]([CH2:37][CH3:38])[CH:34]([CH3:36])C)(C)C.[ClH:39].C(N=C=NC[CH2:46][CH2:47]N(C)C)C.O.ON1[C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][C:56]=2N=N1>ClCCl.CO.ClCCl.C(OCC)(=O)C.CCCCCC>[Cl:1][C:57]1[CH:58]=[C:59]([C:38]2([CH2:46][CH2:47][N:11]3[CH2:10][CH2:9][C:8]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)([C:14]([NH2:16])=[O:15])[CH2:13][CH2:12]3)[CH2:36][CH2:34][N:33]([C:21](=[O:23])[C:20]3[CH:24]=[C:25]([Br:29])[C:26]([O:27][CH3:28])=[C:18]([Br:17])[CH:19]=3)[CH2:37]2)[CH:60]=[CH:61][C:56]=1[Cl:39]

Participants

9

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27580363,5-dibromo-4-methoxybenzoic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 30171294-Phenylpiperidine-4-carboxamide monohydrochloride

Product 1

HCID 44386230HCID 44386230, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolvent2×HCID 21226129Dichloromethane methanolSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Combine 1-[3-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethyl!-4-phenyl-piperidine-4-carboxylic acid amide hydrochloride (241 mg, 0.41 mmol), 3,5-dibromo-4-methoxy -benzoic acid (0.23 g, 0.75 mmol), N,N-diisopropylethylamine (0.75 mmol), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC) (0.75 mmol), and 1-hydroxybenzotriazole hydrate (HOBT) (0.75 g, 1.1 mmol) in dichloromethane (10 mL). After 18 hour, dilute with dichloromethane and extract with 1M hydrochloric acid solution, 5% sodium bicarbonate solution, and water. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with 50% ethyl acetate/hexane and then 6% methanol/dichloromethane to give the title compound: Rf =0.35 (silica gel, 10% methanol/dichloromethane). Exact mass (FAB+): calculated for C32H34Br2Cl2N3O3 calculated 736.0344. Found 736.0330.

Workup

  1. extractionextract with 1M hydrochloric acid solution, 5% sodium bicarbonate solution, and water
  2. dry with materialDry the organic layer over MgSO4
  3. filtrationfilter
  4. customevaporate in vacuo
  5. customto give a residue

Sources & evidence

ORD record
ord-2db972516c80417c9731b0499f1956e5
Source dataset
uspto-grants-1999_01
Patent number
US05861416

Reaction notes

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