Dimethylamine, hydrochloride → 6-Amino-5-chloro-N-[(1-{1-[(dimethylamino)carbonyl]pentyl}piperidin-4-yl)methyl]-2-methoxynicotinamide

HRID 489810Notes

Reaction equation

HRID 489810 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([C:10]([NH:12][CH2:13][CH:14]2[CH2:19][CH2:18][N:17]([CH:20]([CH2:24][CH2:25][CH2:26][CH3:27])[C:21]([OH:23])=O)[CH2:16][CH2:15]2)=[O:11])=[CH:4][C:3]=1[Cl:28].C(P(=O)(OCC)OCC)#N.Cl.[CH3:40][NH:41][CH3:42].C(N(CC)C(C)C)(C)C>CN(C)C=O>[NH2:1][C:2]1[C:3]([Cl:28])=[CH:4][C:5]([C:10]([NH:12][CH2:13][CH:14]2[CH2:15][CH2:16][N:17]([CH:20]([C:21]([N:41]([CH3:42])[CH3:40])=[O:23])[CH2:24][CH2:25][CH2:26][CH3:27])[CH2:18][CH2:19]2)=[O:11])=[C:6]([O:8][CH3:9])[N:7]=1

Participants

6

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 76257Diethyl cyanophosphonateHCID 81531DiisopropylethylamineHCID 222626632-[4-({[(6-Amino-5-chloro-2-methoxypyridin-3-yl)carbonyl]amino}-methyl)piperidine-1-yl]hexanoic acid

Product 1

HCID 222626276-Amino-5-chloro-N-[(1-{1-[(dimethylamino)carbonyl]pentyl}piperidin-4-yl)methyl]-2-methoxynicotinamideYield 10.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[4-({[(6-amino-5-chloro-2-methoxypyridin-3-yl)carbonyl]amino}methyl)piperidine-1-yl]hexanoic acid (500 mg, 1.2 mmol) in dimethylformamide (30 ml) was added diethyl cyanophosphonate (300 mg, 1.8 mmol), N,N-dimethylamine hydrochloride (148 mg, 1.8 mmol) and N,N-diisopropylethylamine (0.63 ml, 3.6 mmol). The mixture was stirred for 72 h at room temperature. The mixture was concentrated in vacuo. The resultant amorphous solid was chromatographed on a column of silica gel eluting with dichloromethane/methanol (20:1) to give 55 mg (10%) of the title compound as a colorless amorphous solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customwas chromatographed on a column of silica gel eluting with dichloromethane/methanol (20:1)

Sources & evidence

ORD record
ord-0919433952e64065a69684769001064b
Source dataset
uspto-grants-2005_12
Patent number
US06979690B2

Reaction notes

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