4-Methoxybenzylamine → 6-Chloro-N-(4-methoxy-benzyl)-nicotinamide

HRID 643684Notes

Reaction equation

HRID 643684 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH2:18])=[CH:15][CH:14]=1.Cl.CN(C)CCCN=C=NCC.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:18][CH2:17][C:16]2[CH:19]=[CH:20][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)=[O:8])=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 754524-MethoxybenzylamineHCID 757711-HydroxybenzotriazoleHCID 792226-Chloronicotinic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 26346576-Chloro-N-(4-methoxy-benzyl)-nicotinamideYield 97.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 6-chloronicotinic acid (473 mg, 3 mmol), 4-methoxybenzylamine (412 mg, 3 mmol), 1-(3-dimethlaminopropyl)-3-ethylcarbodiimide hydrochloride (700 mg, 3.6 mmol) and HOBt (200 mg)) in DMF (15 ml) was stirred at room temperature for 3 h. Water (100 ml) was added. The solution was extracted with ethyl acetate (150ml×2), washed with saturated K2CO3 solution (100 ml) and water (200 ml). Organic layer was dried over Na2SO4 and evaporated under reduced pressure to give the desired product (810 mg, 97%). HPLC (6 minute gradient) tR=3.12 min; MS m/z 275.00, 276.95 (M+H]+

Workup

  1. extractionThe solution was extracted with ethyl acetate (150ml×2)
  2. washwashed with saturated K2CO3 solution (100 ml) and water (200 ml)
  3. dry with materialOrganic layer was dried over Na2SO4
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-344e60c41c3f4be6846e159181e8fd68
Source dataset
uspto-grants-2010_04
Patent number
US07700622B2

Reaction notes

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