Diisopropylethylamine → HCID 90051715, compound

HRID 2284635Notes

Reaction equation

HRID 2284635 reaction equation
[C:1]([NH:8][C@H:9]([C:11]([OH:13])=O)[CH3:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[NH2:46][C:47]1[CH:48]=[C:49]([NH:53][C:54]([C:56]2[C:57]([NH:71][CH2:72][CH2:73][CH3:74])=[N:58][C:59]([NH:62][CH2:63][CH2:64][C:65]3[CH:70]=[CH:69][N:68]=[CH:67][CH:66]=3)=[N:60][CH:61]=2)=[O:55])[CH:50]=[CH:51][CH:52]=1.C(=O)([O-])O.[Na+]>C(OCC)(=O)C.CN(C)C=O>[O:13]=[C:11]([NH:46][C:47]1[CH:52]=[CH:51][CH:50]=[C:49]([NH:53][C:54]([C:56]2[C:57]([NH:71][CH2:72][CH2:73][CH3:74])=[N:58][C:59]([NH:62][CH2:63][CH2:64][C:65]3[CH:66]=[CH:67][N:68]=[CH:69][CH:70]=3)=[N:60][CH:61]=2)=[O:55])[CH:48]=1)[C@@H:9]([NH:8][C:1](=[O:2])[O:3][C:4]([CH3:5])([CH3:6])[CH3:7])[CH3:10]

Participants

9

Reactant 6

HCID 81531DiisopropylethylamineHCID 85082Tert-butoxycarbonylalanineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 90051719HCID 90051719, compound

Product 1

HCID 90051715HCID 90051715, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To N-Boc-L-alanine (57 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (115 mg) and 1-hydroxybenzotriazole monohydrate (81 mg), N,N-dimethylformamide (2 mL) was added at room temperature, and the mixture was stirred at the same temperature for 2 hours. To the reaction mixture, N,N-diisopropylethylamine (153 μL) and N-(3-aminophenyl)-4-(propylamino)-2-((2-(pyridin-4-yl)ethyl)amino)pyrimidine-5-carboxamide (A4, 98 mg) were added at room temperature, and the mixture was stirred at the same temperature for 5 hours. To the reaction mixture, saturated aqueous sodium hydrogencarbonate and ethyl acetate were added. The organic layer was separated, washed with saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (eluent, 98 to 90% ethyl acetate in methanol) to obtain oily (S)-tert-butyl (1-oxo-1-((3-(4-(propylamino)-2-((2-(pyridin-4-yl)ethyl)amino)pyrimidine-5-carboxamido)phenyl)amino)propan-2-yl)carbamate (A5, 137 mg).

Workup

  1. stirringthe mixture was stirred at the same temperature for 5 hours
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by basic silica gel column chromatography (eluent, 98 to 90% ethyl acetate in methanol)

Sources & evidence

ORD record
ord-2b0a843f8c5c4f2989facee3d47cdce0
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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