Sodium Iodide → HCID 10268050, compound

HRID 1251021Notes

Reaction equation

HRID 1251021 reaction equation
C([O:5][C:6](=[O:29])[CH2:7][NH:8][C:9]([C:11]1[C:12]2[N:13]=[C:14]([O:27]C)[C:15]([O:25]C)=[N:16][C:17]=2[CH:18]=[C:19]([N+:22]([O-:24])=[O:23])[C:20]=1[CH3:21])=[O:10])(C)(C)C.[I-].[Na+].Cl[Si](C)(C)C>C(#N)C>[CH3:21][C:20]1[C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:17]2[NH:16][C:15](=[O:25])[C:14](=[O:27])[NH:13][C:12]=2[C:11]=1[C:9]([NH:8][CH2:7][C:6]([OH:29])=[O:5])=[O:10]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 10223000HCID 10223000, compound

Product 1

HCID 10268050HCID 10268050, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred mixture of [(2,3-Dimethoxy-6-methyl-7-nitro-quinoxaline-5-carbonyl)-amino] acetic acid tert-butyl ester (14a) 150 mg (0.37 mmol) and sodium iodide 555 mg (3.7 mmol) in 25 mL acetonitrile is added dropwise chlorotrimethylsilane 0.46 mL (3.7 mmol). After addition was complete, the reaction mixture was refluxed under an atmosphere of nitrogen for 72 hours. The reaction mixture was quenched by pouring into 100 mL water, and the aqueous mixture was concentrated to 10 mL. The residue was mixed with ethyl acetate, and after stirring for 30 minutes, the product precipitated, 35 mg (29%), mp 250° C. (dec.); 1H NMR (DMSO-d6): δ 12.55 (br s, 1H), 8.40 (t, 1H, J=6.3 Hz), 7.84 (s, 1H), 4.07 (d, 2H, J=6.3 Hz), 2.43 (s, 3H); MS (APCI): m/z 323 (M+H).

Workup

  1. additionAfter addition
  2. temperaturethe reaction mixture was refluxed under an atmosphere of nitrogen for 72 hours
  3. customThe reaction mixture was quenched
  4. additionby pouring into 100 mL water
  5. concentrationthe aqueous mixture was concentrated to 10 mL
  6. additionThe residue was mixed with ethyl acetate
  7. customthe product precipitated

Sources & evidence

ORD record
ord-df52677c89e140e7a005e7fae552bc2f
Source dataset
uspto-grants-2002_01
Patent number
US06340758B1

Reaction notes

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