Sodium Carbonate → HCID 24894616, compound

HRID 254747Notes

Reaction equation

HRID 254747 reaction equation
ClC1N=C(NC(C2C=CC3C(=CC=CC=3)C=2)C)N=C(N)N=1.NC(CC1C=CC(B2OC(C)(C)C(C)(C)O2)=CN=1)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+].[NH2:49][CH:50]([CH2:54][C:55]1[CH:60]=[CH:59][C:58]([C:61]2[N:66]=[C:65]([NH2:67])[N:64]=[C:63]([NH:68][CH:69]([C:71]3[CH:80]=[CH:79][C:78]4[C:73](=[CH:74][CH:75]=[CH:76][CH:77]=4)[CH:72]=3)[CH3:70])[N:62]=2)=[CH:57][N:56]=1)[C:51]([OH:53])=[O:52]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.C(#N)C>[NH2:49][C@@H:50]([CH2:54][C:55]1[CH:60]=[CH:59][C:58]([C:61]2[N:66]=[C:65]([NH2:67])[N:64]=[C:63]([NH:68][C@@H:69]([C:71]3[CH:80]=[CH:79][C:78]4[C:73](=[CH:74][CH:75]=[CH:76][CH:77]=4)[CH:72]=3)[CH3:70])[N:62]=2)=[CH:57][N:56]=1)[C:51]([OH:53])=[O:52]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 66653554HCID 66653554, compoundHCID 74338134HCID 74338134, compoundHCID 131728137HCID 131728137, compound

Product 1

HCID 24894616HCID 24894616, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

A microwave vial was charged with 6-chloro-N-[1-naphthalen-2yl-ethyl]-[1,3,5]triazine-2,4-diamine (30 mg, 0.1 mmol), 2-boc protected-amino-3-{5-[4,4,5,5,-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin2-yl-]-propionic acid (50 mg, 0.15 mmol) 1 ml of acetonitrile, and 0.7 ml of water. Aqueous sodium carbonate (0.3 ml; 1N) was added to the solution, followed by 5 mol percent dichlorobis(triphenylphosphine)-palladium(II). The reaction vessel was sealed and heated to 150° C. for 5 minutes by microwave. After cooling, the reaction mixture was evaporated to dryness. The residue was dissolved in 2.5 ml of methanol, and was then purified by Prep-LC to give 7 mg of boc protected 2-amino-3-{5-[4-amino-6-(1-naphthalen-2-yl-ethylamino)-[1,3,5]triazin-2-yl]-pyridin-2-yl}proionic acid.

Workup

  1. customThe reaction vessel was sealed
  2. temperatureAfter cooling
  3. customthe reaction mixture was evaporated to dryness
  4. dissolutionThe residue was dissolved in 2.5 ml of methanol
  5. customwas then purified by Prep-LC
  6. customto give 7 mg of boc

Sources & evidence

ORD record
ord-553bf1199b944833b1d220b77e997056
Source dataset
uspto-grants-2011_01
Patent number
US07875622B2

Reaction notes

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