Triethylamine → HCID 57917645, compound

HRID 1878338Notes

Reaction equation

HRID 1878338 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[Cl:11].[C:12]([NH:16][C:17](=[O:31])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:19]=1)([CH3:15])([CH3:14])[CH3:13].Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C>C(#N)C>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:28]2[CH2:27][CH2:26][N:25]([CH2:24][C:20]3[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=3)[C:17]([NH:16][C:12]([CH3:14])([CH3:15])[CH3:13])=[O:31])[CH2:30][CH2:29]2)=[O:8])=[CH:4][C:3]=1[Cl:11]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 172114-Amino-3-chlorobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66877987N-tert-butyl-3-(piperazin-1-ylmethyl)benzamide

Product 1

HCID 57917645HCID 57917645, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Amino-3-chlorobenzoic acid (1.04 g, 6.06 mmol), N-tert-butyl-3-(piperazin-1-ylmethyl)-benzamide (888 mg, 3.22 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydro-chloride (1.742 g, 9.09 mmol) and triethylamine (1.23 g, 1.69 mL, 12.12 mmol) were combined and stirred in acetonitrile (20 mL) at room temperature overnight (under nitrogen). The reaction was concentrated under reduced pressure and the residue was diluted with dichloromethane (30 mL) and water. The organic layer was separated, dried over sodium sulfate and concentrated under vacuum. The resulting residue was purified by silica chromatography (eluting with a solvent gradient from dichloromethane to 4% methanol/dichloromethane) to afford the title compound (1.3 g).

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. additionthe residue was diluted with dichloromethane (30 mL) and water
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe resulting residue was purified by silica chromatography (
  7. washeluting with a solvent gradient from dichloromethane to 4% methanol/dichloromethane)

Sources & evidence

ORD record
ord-a673eb3026c34c888a7b2504f1633daf
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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