HCID 178490100, compound → HCID 178479338, compound

HRID 1296463Notes

Reaction equation

HRID 1296463 reaction equation
Cl.C[O:3][C:4]1[CH:9]=[C:8]([O:10]C)[CH:7]=[CH:6][C:5]=1[CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([NH:19][C:20]([C:22]1[C:27]([NH2:28])=[N:26][C:25]([NH2:29])=[C:24]([Cl:30])[N:23]=1)=[O:21])=[NH:18]>Br>[ClH:30].[OH:3][C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:5]=1[CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([NH:19][C:20]([C:22]1[C:27]([NH2:28])=[N:26][C:25]([NH2:29])=[C:24]([Cl:30])[N:23]=1)=[O:21])=[NH:18]

Participants

3

Reactant 1

HCID 178490100HCID 178490100, compound

Product 1

HCID 178479338HCID 178479338, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A vigorously stirred solution of 80 (290 mg, 0.63 mmol) in 48% HBr (20 mL) was refluxed for 4 h and then cooled. The solvent was removed at reduced pressure and the material was purified by column chromatography (silica gel, 4:1:0.1 chloroform/ethanol/concentrated ammonium hydroxide). The fractions with product were collected and the solvent was removed under reduced pressure. The residue was treated with 3% HCl, washed with water (2×5 mL) and dried to provide 81 (79 mg, 32%) as a yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 1.54 (s, 4H), 2.43 (br s, 2H), 3.31 (br s, 2H), 6.12 (d, 1H), 6.32 (s, 1H), 6.78 (d, 1H), 8.86 (br s, 1H), 8.99 (br s, 1H), 9.28 (s, 1H), 10.56 (s, 1H). APCI MS m/z 394 [C16H20ClN7O3+H]+.

Workup

  1. temperaturecooled
  2. customThe solvent was removed at reduced pressure
  3. customthe material was purified by column chromatography (silica gel, 4:1:0.1 chloroform/ethanol/concentrated ammonium hydroxide)
  4. customThe fractions with product were collected
  5. customthe solvent was removed under reduced pressure
  6. additionThe residue was treated with 3% HCl
  7. washwashed with water (2×5 mL)
  8. customdried

Sources & evidence

ORD record
ord-026404c50ba24519b4d632d798530ee2
Source dataset
uspto-grants-2007_07
Patent number
US07247636B2

Reaction notes

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