3-Pyridinemethanamine → 6-Chloro-4-(pyridin-3-ylmethylamino)nicotinamide

HRID 384280

Reaction equation

HRID 384280 reaction equation
Cl[C:2]1[C:7]([C:8]([NH2:10])=[O:9])=[CH:6][N:5]=[C:4]([Cl:11])[CH:3]=1.[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][NH2:19])[CH:13]=1.CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[Cl:11][C:4]1[CH:3]=[C:2]([NH:19][CH2:18][C:14]2[CH:13]=[N:12][CH:17]=[CH:16][CH:15]=2)[C:7]([C:8]([NH2:10])=[O:9])=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 310183-PyridinemethanamineHCID 81531DiisopropylethylamineHCID 6000444,6-Dichloronicotinamide

Product 1

HCID 584402016-Chloro-4-(pyridin-3-ylmethylamino)nicotinamideYield 82.6%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4,6-Dichloronicotinamide (1, 950 mg, 5 mmoles), 3-picolylamine (756 mg, 7 mmoles) and DIEA (12 mmoles) in NMP (5 mL) was stirred at 60° C. for 20 hrs. The reaction mixture was concentrated under an oil pump. The residue was washed with water and dried under an oil pump. The desired 6-chloro-4-(pyridin-3-ylmethylamino)nicotinamide (2, 1.085 g) was obtained. MS+: 263.1, UV: λ=220.9; 260.9 nm. 1H NMR: (CDCl3) δ8.96 (s, 1H), δ8.60 (s, 1H), δ8.57 (d, J=3.2 Hz, 1H), δ8.30 (s, 1H), δ7.64 (d, J=7.6Hz, 1H), δ7.31 (dd, J1=7.6Hz, J2=3.2Hz, 1H), δ6.51 (s, 1H), δ5.80 (b, 2H), δ4.47 (s, 1H), δ4.45 (s, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated under an oil pump
  2. washThe residue was washed with water
  3. customdried under an oil pump

Sources & evidence

ORD record
ord-f017a64b08b7473796103d5d7ea4d099
Source dataset
uspto-grants-2013_02
Patent number
US08367689B2

Linked notes

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