Aniline → HCID 178456581, compound

HRID 892102Notes

Reaction equation

HRID 892102 reaction equation
[ClH:1].[Cl:2][CH2:3][CH:4]1[CH2:15][N:14]2[C:6]([C:7]3[NH:8][C:9]([CH:20]4[CH2:24][CH2:23][CH2:22][CH2:21]4)=[N:10][C:11]=3[N:12]([CH2:17][CH2:18][CH3:19])[C:13]2=[O:16])=[N:5]1.[NH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(=O)([O-])O.[Na+]>O>[ClH:2].[ClH:1].[CH:20]1([C:9]2[NH:8][C:7]3[C:6]4=[N:5][CH:4]([CH2:3][NH:25][C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[CH2:15][N:14]4[C:13](=[O:16])[N:12]([CH2:17][CH2:18][CH3:19])[C:11]=3[N:10]=2)[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 6115AnilineHCID 516892Sodium BicarbonateHCID 178456575HCID 178456575, compound

Product 1

HCID 178456581HCID 178456581, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
70 °C

Procedure

To Compound 26 (12 mg, 0.04 mmol) obtained in Example 26 were added water (3 mL), aniline (20 mg, 0.24 mmol, 6.0 equivalents) and sodium hydrogen carbonate (62 mg, 0.74 mmol, 18.5 equivalents), and the mixture was stirred with heating at 70° C. for 2 hours. To the reaction solution was added water, the mixture was extracted with ethyl acetate, and the extract was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (chloroform:methanol=95:5), to the product was added a 4 mol/L solution of hydrogen chloride in ethyl acetate, and then the mixture was concentrated. The residue was crystallized from acetone and methanol to obtain the title compound (3 mg, 19%) as a light yellow solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washthe extract was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (chloroform:methanol=95:5), to the product
  6. additionwas added a 4 mol/L solution of hydrogen chloride in ethyl acetate
  7. concentrationthe mixture was concentrated
  8. customThe residue was crystallized from acetone and methanol

Sources & evidence

ORD record
ord-6af4c239723b4c5e91ad52b7740ec555
Source dataset
uspto-grants-2006_02
Patent number
US07005430B2

Reaction notes

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