Benzylamine → HCID 117892046, compound

HRID 930545Notes

Reaction equation

HRID 930545 reaction equation
Cl[C:2]1[CH:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.CCN(C(C)C)C(C)C.[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[CH3:29][N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1>CN1C(=O)CCC1>[CH2:21]([NH:28][C:6]1[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=[C:2]([N:33]2[CH2:34][CH2:35][N:30]([CH3:29])[CH2:31][CH2:32]2)[CH:7]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 122757652,4-Dichloro-5-nitropyridine

Product 1

HCID 117892046HCID 117892046, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 2,4-dichloro-5-nitro-pyridine E-2.1″ (5.000 g; 25.908 mmol) in NMP are added DIPEA (8.372 ml, 51.817 mmol) and benzylamine (3.054 ml, 28.499 mmol). The mixture is stirred for 1 h at RT. 1-Methylpiperazine (3.172 ml; 28.499 mmol) is then added and the mixture is stirred at 50° C. overnight. The residue is loaded onto isolute, split into 5 portions and purified using the basic preparatory reversed phase chromatography (method: prep. HPLC1). Product containing fractions are combined and freeze-dried (yield: 66%, 5.619 g; 17.163 mmol)

Workup

  1. stirringthe mixture is stirred at 50° C. overnight
  2. customsplit into 5 portions
  3. custompurified
  4. additionProduct containing fractions
  5. customfreeze-dried (yield: 66%, 5.619 g; 17.163 mmol)

Sources & evidence

ORD record
ord-afe407f9d6974f9094ddbe26116574bf
Source dataset
uspto-grants-2016_03
Patent number
US09296748B2

Reaction notes

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