Benzoyl chloride → HCID 68525732, compound

HRID 1932517Notes

Reaction equation

HRID 1932517 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:41]=[CH:42][C:43]=1[Cl:44])[C:5]([NH:7][C:8]1[CH:9]=[N:10][C:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23](=[O:40])[N:24]3[CH2:29][CH2:28][N:27]([CH2:30][C:31]4[CH:39]=[CH:38][C:37]5[O:36][CH2:35][O:34][C:33]=5[CH:32]=4)[CH2:26][CH2:25]3)=[CH:17][CH:16]=2)=[CH:12][CH:13]=1)=[O:6].C(N(CC)CC)C.[C:52](Cl)(=[O:59])[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1.O.O.[C:63]([OH:68])(=[O:67])[C:64]([OH:66])=[O:65]>C1COCC1.C(O)(C)C.O>[C:63]([OH:68])(=[O:67])[C:64]([OH:66])=[O:65].[C:52]([N:14]([C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23](=[O:40])[N:24]2[CH2:25][CH2:26][N:27]([CH2:30][C:31]3[CH:39]=[CH:38][C:37]4[O:36][CH2:35][O:34][C:33]=4[CH:32]=3)[CH2:28][CH2:29]2)=[CH:17][CH:16]=1)[C:11]1[N:10]=[CH:9][C:8]([NH:7][C:5](=[O:6])[C:4]2[CH:41]=[CH:42][C:43]([Cl:44])=[C:2]([Cl:1])[CH:3]=2)=[CH:13][CH:12]=1)(=[O:59])[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1

Participants

8

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 61373Oxalic acid dihydrateHCID 68523688HCID 68523688, compound

Product 1

HCID 68525732HCID 68525732, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3,4-dichloro-N-(6-{4-[3-oxo-3-(4-piperonylpiperazin-1-yl)propyl]phenylamino}-pyridin-3-yl)benzamide (250 mg, 0.395 mmol) in THF (5 mL) were added triethylamine (0.132 mL, 0.949 mmol) and benzoyl chloride (0.0550 mL, 0.474 mmol), and the resulting solution was stirred for 7 hours at room temperature. Water was added to the resulting reaction solution, and extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried over anhydrous magnesium sulfate, and evaporated. The residue was purified by silica gel column chromatography (dichloromethane:methanol=10:1) to yield 0.300 g of a free form. To this free form were added isopropanol (5 mL) and oxalic acid dihydrate (100 mg, 0.793 mmol), and the resulting solution was dissolved under heat. The solvent was evaporated, and the resulting solid was recrystallized from isopropanol, to thereby yield 80.0 mg of the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by silica gel column chromatography (dichloromethane:methanol=10:1)
  6. customto yield 0.300 g of a free form
  7. dissolutionthe resulting solution was dissolved
  8. temperatureunder heat
  9. customThe solvent was evaporated
  10. customthe resulting solid was recrystallized from isopropanol

Sources & evidence

ORD record
ord-7e00a9b13b41461aabf4f17178ef2528
Source dataset
uspto-grants-2012_05
Patent number
US08188277B2

Reaction notes

Loading…