4-Methylmorpholine → HCID 20738635, compound

HRID 354100

Reaction equation

HRID 354100 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[C:33]([O:37][C:38](=[O:49])[NH:39][CH2:40][C:41]1[CH:46]=[CH:45][C:44]([CH2:47][NH2:48])=[CH:43][CH:42]=1)([CH3:36])([CH3:35])[CH3:34].CN1CCOCC1>CN(C)C=O>[C:33]([O:37][C:38](=[O:49])[NH:39][CH2:40][C:41]1[CH:42]=[CH:43][C:44]([CH2:47][NH:48][C:4]([C:3]2[C:2]([Cl:1])=[N:10][CH:9]=[CH:8][CH:7]=2)=[O:6])=[CH:45][CH:46]=1)([CH3:36])([CH3:34])[CH3:35]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 762582-Chloronicotinic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 3354775tert-butyl N-{[4-(aminomethyl)phenyl]methyl}carbamate

Product 1

HCID 20738635HCID 20738635, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Chloro-nicotinic acid (2.86 g, 18.2 mmol), 1-hydroxybenzotriazole (3.0 g, 21.8 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (4.18 g, 21.8 mmol) were dissolved in N,N-dimethylformamide (50 ml) at room temperature and (4-aminomethyl-benzyl)-carbamic acid tert-butyl ester (4.29 g, 18.2 mmol) (see Preparation 1) added followed by addition of N-methyl morpholine (4 ml, 36.3 mmol). The reaction mixture was stirred under an atmosphere of nitrogen at room temperature for 18 hours, then partitioned between ethyl acetate (100 ml) and water (100 ml) and the organic layer separated. The organic layer was then washed with a saturated aqueous solution of sodium chloride (100 ml), dried over anhydrous magnesium sulphate and the solvent removed in vacuo. The residue was then triturated with diethylether (2-fold 10 ml) to give (4-{[(2-chloro-pyridine-3-carbonyl)-amino]-methyl}-benzyl)-carbamic acid tert-butyl ester (6.71 g) as a white solid.

Workup

  1. custompartitioned between ethyl acetate (100 ml) and water (100 ml)
  2. customthe organic layer separated
  3. washThe organic layer was then washed with a saturated aqueous solution of sodium chloride (100 ml)
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customthe solvent removed in vacuo
  6. customThe residue was then triturated with diethylether (2-fold 10 ml)

Sources & evidence

ORD record
ord-64f729534280458b9a3bfb1aa91f6126
Source dataset
uspto-grants-2004_06
Patent number
US06756392B2

Linked notes

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