Sodium Bicarbonate → HCID 72191180, compound

HRID 2284637Notes

Reaction equation

HRID 2284637 reaction equation
[NH2:1][C@@H:2]([CH3:34])[C:3]([NH:5][C:6]1[CH:7]=[C:8]([NH:12][C:13]([C:15]2[C:16]([NH:30][CH2:31][CH2:32][CH3:33])=[N:17][C:18]([NH:21][CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)=[N:19][CH:20]=2)=[O:14])[CH:9]=[CH:10][CH:11]=1)=[O:4].Cl.[CH3:36][N:37]([CH3:44])[CH2:38]/[CH:39]=[CH:40]/[C:41](O)=[O:42].Cl.C(N=C=NCCCN(C)C)C.C(=O)([O-])O.[Na+]>CN(C)C=O.C(N(CC)CC)C.C(OCC)(=O)C>[CH3:36][N:37]([CH3:44])[CH2:38]/[CH:39]=[CH:40]/[C:41]([NH:1][C@@H:2]([CH3:34])[C:3]([NH:5][C:6]1[CH:7]=[C:8]([NH:12][C:13]([C:15]2[C:16]([NH:30][CH2:31][CH2:32][CH3:33])=[N:17][C:18]([NH:21][CH2:22][CH2:23][C:24]3[CH:25]=[CH:26][N:27]=[CH:28][CH:29]=3)=[N:19][CH:20]=2)=[O:14])[CH:9]=[CH:10][CH:11]=1)=[O:4])=[O:42]

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 45358758(2E)-4-(Dimethylamino)-2-butenoic acid hydrochlorideHCID 90052192HCID 90052192, compound

Product 1

HCID 72191180HCID 72191180, compoundYield 42.2%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (S)—N-(3-(2-aminopropanamido)phenyl)-4-(propylamino)-2-((2-(pyridin-4-yl)ethyl)amino)pyrimidine-5-carboxamide (A6, 21 mg), 4-dimethylaminocrotonic acid hydrochloride (16 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (38 mg) in N,N-dimethylformamide (2 mL), triethylamine (40 μL) was added at room temperature, and the mixture was stirred at 50° C. for 30 minutes. The reaction mixture was cooled to room temperature, and then saturated aqueous sodium hydrogencarbonate and ethyl acetate were added to the mixture. The organic layer was separated, washed with water, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 95% chloroform/5% methanol) to obtain (S,E)-N-(3-(2-(4-(dimethylamino)-2-butenamido)propanamido)phenyl)-4-(propylamino)-2-((2-(pyridin-4-yl)ethyl)amino)pyrimidine-5-carboxamide (1-2, 11 mg).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (eluent, 95% chloroform/5% methanol)

Sources & evidence

ORD record
ord-fa71cf37371a4529bfdad9aa17ed98d3
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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