Diisopropylethylamine → N-[6-(4-ethylpiperazin-1-yl)pyrid-3-yl]-2-chloro-5-(2-morpholinopyrid-4-ylcarbonylamino)benzamide

HRID 1007135Notes

Reaction equation

HRID 1007135 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[CH:19]=[CH:18][N:17]=[C:16]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[CH:15]=2)=[O:13])=[CH:7][C:3]=1[C:4](O)=[O:5].[NH2:26][C:27]1[CH:28]=[CH:29][C:30]([N:33]2[CH2:38][CH2:37][N:36]([CH2:39][CH3:40])[CH2:35][CH2:34]2)=[N:31][CH:32]=1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH2:39]([N:36]1[CH2:35][CH2:34][N:33]([C:30]2[N:31]=[CH:32][C:27]([NH:26][C:4](=[O:5])[C:3]3[CH:7]=[C:8]([NH:11][C:12]([C:14]4[CH:19]=[CH:18][N:17]=[C:16]([N:20]5[CH2:25][CH2:24][O:23][CH2:22][CH2:21]5)[CH:15]=4)=[O:13])[CH:9]=[CH:10][C:2]=3[Cl:1])=[CH:28][CH:29]=2)[CH2:38][CH2:37]1)[CH3:40]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 91616746-(4-Ethylpiperazin-1-yl)pyridin-3-amineHCID 226677762-Chloro-5-(2-morpholinopyrid-4-ylcarbonylamino)benzoic acid

Product 1

HCID 9828992N-[6-(4-ethylpiperazin-1-yl)pyrid-3-yl]-2-chloro-5-(2-morpholinopyrid-4-ylcarbonylamino)benzamideYield 28.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Chloro-5-(2-morpholinopyrid-4-ylcarbonylamino)benzoic acid (0.162 g) was added to a stirred mixture of 5-amino-2-(4-ethylpiperazin-1-yl)pyridine (0.093 g), diisopropylethylamine (0.232 g), 2-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate(V) (0.176 g) and DMF (10 ml) and the mixture was stirred at ambient temperature for 16 hours. The mixture was partitioned between ethyl acetate and water. The organic phase was washed with a saturated aqueous sodium bicarbonate solution and evaporated. The residue was triturated under a mixture of isohexane and ethyl acetate. The resultant solid was isolated and dried under vacuum at 40° C. to give the title compound (0.071 g); NMR Spectrum: (DMSOd6) 1.02 (t, 3H), 2.34 (m, 2H), 2.4-2.46 (m, 4H), 3.38-3.42 (m, 4H), 3.5-3.53 (m, 4H), 3.69-3.71 (m, 4H), 6.82 (d, 1H), 7.08 (d, 2H), 7.22 (s, 1H), 7.62 (d, 1H), 7.82-7.98 (m, 3H), 8.28 (d, 1H), 8.39 (s, 1H); Mass Spectrum: M+H+ 550 and 552.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washThe organic phase was washed with a saturated aqueous sodium bicarbonate solution
  3. customevaporated
  4. customThe residue was triturated under a mixture of isohexane and ethyl acetate
  5. customThe resultant solid was isolated
  6. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-c143823d779f4e60b0c9a198fe760d6d
Source dataset
uspto-grants-2004_09
Patent number
US06794380B2

Reaction notes

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