Water → N-[3-(dimethylamino)propyl]-5-iodo-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide

HRID 2089261Notes

Reaction equation

HRID 2089261 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([C:20](O)=[O:21])[C:5](=[O:19])[N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[C:7]=1[CH3:8].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:35][N:36]([CH3:41])[CH2:37][CH2:38][CH2:39][NH2:40].O>CN(C=O)C>[CH3:35][N:36]([CH3:41])[CH2:37][CH2:38][CH2:39][NH:40][C:20]([C:4]1[C:5](=[O:19])[N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:16])([F:18])[F:17])[CH:10]=2)[C:7]([CH3:8])=[C:2]([I:1])[CH:3]=1)=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 7993N,N-Dimethyl-1,3-propanediamineHCID 682631,1'-CarbonyldiimidazoleHCID 582180465-Iodo-6-methyl-2-oxo-1-(3-(trifluoromethyl)phenyl)-1,2-dihydropyridine-3-carboxylic acid

Product 1

HCID 58218051N-[3-(dimethylamino)propyl]-5-iodo-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamideYield 83.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of 5-iodo-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxylic acid (10 g, 23.64 mmol) in DMF (20 mL) was added a solution of carbonyldiimidazole (5.14 g, 30.72 mmol) in DMF (30 mL) over a period of 40 min at 25° C. After stirring the mixture for 30 minutes, was added a solution of N,N-dimethylpropane-1,3-diamine (3.62 g, 35.45 mmol) in DMF (10 mL) over a period of 20 min at 25° C. and stirred for 40 minutes. After completion of the reaction, water (100 mL) was charged at 25° C. over a period of 1 h. The resulting suspension was stirred for 4 h and filtered. The cake was washed with water (50 mL) and dried under vacuum at 50° C. for 12 h to afford the title product as a light brown solid (10 g, 83%); 1H NMR (400 MHz, CDCl3) δ 9.36 (bs, 1 H), 8.87 (s, 1 H), 7.82 (d, J=7.53 Hz, 1 H), 7.76 (t, J=7.78Hz, 1 H), 7.49 (s, 1 H), 7.41 (d, J=8.03 Hz, 1 H), 3.43 (q, J=6.86 Hz, 2 H), 2.30-2.35 (m, 2 H), 2.29 (s, 3 H), 2.20 (s, 6 H), 1.74 (p, J=7.28 Hz, 2 H); LCMSm/z: 508 [M+].

Workup

  1. stirringstirred for 40 minutes
  2. additionwas charged at 25° C. over a period of 1 h
  3. stirringThe resulting suspension was stirred for 4 h
  4. filtrationfiltered
  5. washThe cake was washed with water (50 mL)
  6. customdried under vacuum at 50° C. for 12 h

Sources & evidence

ORD record
ord-633367eab68643efb7fc47c4c3b398b7
Source dataset
uspto-grants-2013_05
Patent number
US08436024B2

Reaction notes

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