Sodium Bicarbonate → (S,E)-2-((4-cyanophenyl)amino)-N-(3-(2-(4-(dimethylamino)-N-methyl-2-butenamido)propanamido)phenyl)-4-(propylamino)pyrimidine-5-carboxamide

HRID 2284695Notes

Reaction equation

HRID 2284695 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[N:15]=[C:14]([NH:16][CH2:17][CH2:18][CH3:19])[C:13]([C:20]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([NH:29][C:30](=[O:35])[C@@H:31]([NH:33][CH3:34])[CH3:32])[CH:24]=3)=[O:21])=[CH:12][N:11]=2)=[CH:5][CH:4]=1)#[N:2].Cl.[CH3:37][N:38]([CH3:45])[CH2:39]/[CH:40]=[CH:41]/[C:42](O)=[O:43].Cl.C(N=C=NCCCN(C)C)C.C(=O)([O-])O.[Na+]>CN(C)C=O.C(N(CC)C(C)C)(C)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[N:15]=[C:14]([NH:16][CH2:17][CH2:18][CH3:19])[C:13]([C:20]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([NH:29][C:30](=[O:35])[C@@H:31]([N:33]([CH3:34])[C:42](=[O:43])/[CH:41]=[CH:40]/[CH2:39][N:38]([CH3:45])[CH3:37])[CH3:32])[CH:24]=3)=[O:21])=[CH:12][N:11]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 45358758(2E)-4-(Dimethylamino)-2-butenoic acid hydrochlorideHCID 90053313(S)-2-((4-cyanophenyl)amino)-N-(3-(2-(methylamino)propanamido)phenyl)-4-(propylamino)pyrimidine-5-carboxamide

Product 1

HCID 117857077(S,E)-2-((4-cyanophenyl)amino)-N-(3-(2-(4-(dimethylamino)-N-methyl-2-butenamido)propanamido)phenyl)-4-(propylamino)pyrimidine-5-carboxamideYield 57.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 81531DiisopropylethylamineSolvent

Procedure

To a solution of (S)-2-((4-cyanophenyl)amino)-N-(3-(2-(methylamino)propanamido)phenyl)-4-(propylamino)pyrimidine-5-carboxamide (E1) dihydrochloride (58 mg), 4-dimethylaminocrotonic acid hydrochloride (33 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (38 mg) in N,N-dimethylformamide (1 mL), N,N-diisopropylethylamine (174 μL) was added at room temperature, and the mixture was stirred at the same temperature for 15 hours. To the reaction mixture, saturated aqueous sodium hydrogencarbonate was added. The solid matter was taken by filtration, washed with water, and then dried under reduced pressure. The obtained solid matter was purified by basic silica gel column chromatography (eluent, 98 to 88% ethyl acetate in methanol) to obtain (S,E)-2-((4-cyanophenyl)amino)-N-(3-(2-(4-(dimethylamino)-N-methyl-2-butenamido)propanamido)phenyl)-4-(propylamino)pyrimidine-5-carboxamide (6-1, 41 mg) as white solid.

Workup

  1. filtrationThe solid matter was taken by filtration
  2. washwashed with water
  3. customdried under reduced pressure
  4. customThe obtained solid matter was purified by basic silica gel column chromatography (eluent, 98 to 88% ethyl acetate in methanol)

Sources & evidence

ORD record
ord-79c3043f1ef543148e543112e274fc24
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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