Triethylamine → 3-[3-Chloro-3'-(4-methyl-piperazine-1-carbonyl)-biphenyl-4-ylmethyl]-1-cyclohexyl-pyrrolidin-2-one hydrochloride salt

HRID 2235280Notes

Reaction equation

HRID 2235280 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27](O)=[O:28])[CH:22]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][CH:9]1[CH2:13][CH2:12][N:11]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[C:10]1=[O:20].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.[CH3:59][N:60]1[CH2:65][CH2:64][NH:63][CH2:62][CH2:61]1>CN(C=O)C.O>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([N:63]3[CH2:64][CH2:65][N:60]([CH3:59])[CH2:61][CH2:62]3)=[O:28])[CH:22]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][CH:9]1[CH2:13][CH2:12][N:11]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[C:10]1=[O:20]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59299302HCID 59299302, compound

Product 1

HCID 684704113-[3-Chloro-3'-(4-methyl-piperazine-1-carbonyl)-biphenyl-4-ylmethyl]-1-cyclohexyl-pyrrolidin-2-one hydrochloride salt

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Charge a vial with 3′-chloro-4′-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-biphenyl-3-carboxylic acid (Example 7) (70 mg, 0.17 mmol), EDCl (2.0 eq.) and HOBt (1.0 eq.). Dissolve in DMF (0.1 M) and add triethylamine (4.0 eq.) and N-methyl piperazine (34 mg, 0.34 mmol) (2.0 eq). Stir at room temperature overnight. Pour into water and extract with ether. Dry over sodium sulfate, filter and concentrate. Purify over silica gel. Dissolve the residue in methylene chloride and acidify with 4N HCl in dioxane. Concentrate in vacuo. Mass spec (apci) m/z=494.3 (M+H-HCl).

Workup

  1. extractionextract with ether
  2. dry with materialDry over sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify over silica gel
  6. dissolutionDissolve the residue in methylene chloride
  7. concentrationConcentrate in vacuo

Sources & evidence

ORD record
ord-e3d9ef59b4b943ba8e274f9e10342a0e
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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