HCID 135506364, compound → HCID 135430974, compound

HRID 1355562Notes

Reaction equation

HRID 1355562 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([S:9]([C:12]2[CH:13]=[CH:14][C:15]([O:37][CH2:38][CH2:39][CH3:40])=[C:16]([C:18]3[NH:19][C:20](=[O:36])[C:21]4[N:22]([C:27]5[CH:32]=[CH:31][C:30]([N+:33]([O-])=O)=[CH:29][CH:28]=5)[CH:23]=[N:24][C:25]=4[N:26]=3)[CH:17]=2)(=[O:11])=[O:10])[CH2:5][CH2:4]1)[CH3:2]>C(O)(=O)C.O.[Fe]>[NH2:33][C:30]1[CH:31]=[CH:32][C:27]([N:22]2[C:21]3[C:20](=[O:36])[NH:19][C:18]([C:16]4[CH:17]=[C:12]([S:9]([N:6]5[CH2:5][CH2:4][N:3]([CH2:1][CH3:2])[CH2:8][CH2:7]5)(=[O:10])=[O:11])[CH:13]=[CH:14][C:15]=4[O:37][CH2:38][CH2:39][CH3:40])=[N:26][C:25]=3[N:24]=[CH:23]2)=[CH:28][CH:29]=1

Participants

5

Reactant 1

HCID 135506364HCID 135506364, compound

Product 1

HCID 135430974HCID 135430974, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Iron powder (137 mg, 2.45 mmol) was added to a solution of 2-[5-(4-ethylpiperazin-1-ylsulfonyl)-2-n-propoxyphenyl]-7-(4-nitrophenyl)purin-6-one (Example 11; 110 mg, 0.19 mmol) in acetic acid (2.2 mL) and water (100 μL), and the reaction stirred vigorously at room temperature for 3 hours. The mixture was filtered through Celite®, washing well with ethyl acetate, and the filtrate concentrated under reduced pressure. The residue was partitioned between ethyl acetate and sodium bicarbonate solution, the layers separated, and the organic phase dried (MgSO4) and evaporated under reduced pressure to give the title compound (80 mg, 79%).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. washwashing well with ethyl acetate
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customThe residue was partitioned between ethyl acetate and sodium bicarbonate solution
  5. customthe layers separated
  6. dry with materialthe organic phase dried (MgSO4)
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-30e0865ba54c4c5980d5adb49de8a2fd
Source dataset
uspto-grants-2003_07
Patent number
US06586439B2

Reaction notes

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