Di(succinimido) carbonate → HCID 58577244, compound

HRID 587457Notes

Reaction equation

HRID 587457 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]2[C:23]([NH2:24])=[CH:22][N:21]=[CH:20][N:19]=2)=[CH:13][CH:12]=1.C1C(=O)N(OC(ON2C(=O)CCC2=O)=O)[C:27](=[O:28])C1>CN(C=O)C.O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[C:27](=[O:28])[NH:24][C:23]3[C:18]2=[N:19][CH:20]=[N:21][CH:22]=3)=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 676246Di(succinimido) carbonateHCID 70162511N4-[4-(1,3-benzoxazol-2-ylamino)phenyl]pyrimidine-4,5-diamine

Product 1

HCID 58577244HCID 58577244, compoundYield 31.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of N4-[4-(1,3-benzoxazol-2-ylamino)phenyl]pyrimidine-4,5-diamine (55 mg) and bis(2,5-dioxopyrrolidin-1-yl)carbonate (53 mg) in DMF (5 mL) was stirred overnight at 80° C. then at 95° C. for 3 h. After this time, the reaction mixture was cooled to ambient temperature, diluted with water (50 mL) and extracted with ethyl acetate (100 mL). The organic layer was washed with water (50 mL), 5% aqueous lithium chloride (50 mL) then brine (50 mL), dried over sodium sulfate, and filtered and the filtrate was concentrated under reduced pressure. The residue obtained was purified by chromatography (silica, methylene chloride to 1:9 methanol/methylene chloride), solvent exchanged with acetonitrile and freeze dried from acetonitrile/water to afford 9-[4-(1,3-benzoxazol-2-ylamino)phenyl]-7,9-dihydro-8H-purin-8-one (19 mg) as off-white crystals.

Workup

  1. waitat 95° C. for 3 h
  2. temperatureAfter this time, the reaction mixture was cooled to ambient temperature
  3. extractionextracted with ethyl acetate (100 mL)
  4. washThe organic layer was washed with water (50 mL), 5% aqueous lithium chloride (50 mL)
  5. dry with materialbrine (50 mL), dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue obtained
  9. customwas purified by chromatography (silica, methylene chloride to 1:9 methanol/methylene chloride), solvent
  10. dry with materialdried from acetonitrile/water

Sources & evidence

ORD record
ord-a511c466d36c4518be05e9f3412800d6
Source dataset
uspto-grants-2016_01
Patent number
US09226921B2

Reaction notes

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