Water → HCID 178515168, compound

HRID 1400111Notes

Reaction equation

HRID 1400111 reaction equation
[CH2:1]([N:9]1[C:17](=[O:18])[C:16]2[C:11](=[C:12]3[CH:21]=[N:20][NH:19][C:13]3=[N:14][CH:15]=2)[C:10]1=[O:22])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1C(=O)N([Br:30])C(=O)C1.O>C(Cl)Cl>[Br:30][C:21]1[C:12]2[C:13](=[N:14][CH:15]=[C:16]3[C:17](=[O:18])[N:9]([CH2:1][CH2:2][C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=4)[C:10](=[O:22])[C:11]3=2)[NH:19][N:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 469095657-phenethylpyrazolo[3,4-b]pyrrolo[3,4-d]pyridine-6,8(3H,7H)-dione

Product 1

HCID 178515168HCID 178515168, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-phenethylpyrazolo[3,4-b]pyrrolo[3,4-d]pyridine-6,8(3H,7H)-dione (1 g, 3.4 mmol) in CH2Cl2 (15 mL), freshly recrystallised NBS (0.66 g, 3.76 mmol) was added and the reaction was stirred at room temperature for 3 h. The reaction was monitored by TLC, and on completion of the reaction; water (50 mL) was added and the reaction mixture was extracted with EtOAc (3×100 mL). The combined EtOAc layer was dried over sodium sulphate and evaporated under vacuo to give a residue which was purified by column chromatography (silica gel, gradient 0-10% EtOAc in a solution of 60:40 hexane and chloroform) to afford 1-bromo-7-phenethylpyrazolo[3,4-b]pyrrolo[3,4-d]pyridine-6,8(3H,7H)-dione (1 g, 79%) as a solid. 1HNMR (400 MHz, DMSO-d6) δ: 14.80 (s, 1H), 8.01 (s, 1H), 7.15-7.35 (m, 5H), 3.85 (t, 2H), 2.95 (t, 2H); LCMS: [M+H] 371.

Workup

  1. customon completion of the reaction
  2. extractionthe reaction mixture was extracted with EtOAc (3×100 mL)
  3. dry with materialThe combined EtOAc layer was dried over sodium sulphate
  4. customevaporated under vacuo
  5. customto give a residue which
  6. customwas purified by column chromatography (silica gel, gradient 0-10% EtOAc in a solution of 60:40 hexane and chloroform)

Sources & evidence

ORD record
ord-fbc59987b9e04aecbd24e3fcf0bab1d4
Source dataset
uspto-grants-2014_12
Patent number
US08906928B2

Reaction notes

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