Water → HCID 58001181, compound

HRID 658040Notes

Reaction equation

HRID 658040 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][C:16]([O:18]C2C=CC=CC=2)=O)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25]([O:29][C:30]([NH:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[NH:39][C:40](=[O:55])[C:41]1[CH:46]=[CH:45][C:44]([CH2:47][NH:48][CH2:49][CH2:50][CH2:51][N:52]([CH3:54])[CH3:53])=[CH:43][CH:42]=1)=[O:31])([CH3:28])([CH3:27])[CH3:26].O>CS(C)=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([NH:15][C:16](=[O:18])[N:48]([CH2:47][C:44]2[CH:45]=[CH:46][C:41]([C:40]([NH:39][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=3[NH:32][C:30]([O:29][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:31])=[O:55])=[CH:42][CH:43]=2)[CH2:49][CH2:50][CH2:51][N:52]([CH3:53])[CH3:54])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 57656651HCID 57656651, compoundHCID 58001225HCID 58001225, compound

Product 1

HCID 58001181HCID 58001181, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1-Benzyloxy-3-(phenoxycarbonylamino)benzene (Reference Compound No. 5-1, 3.7 g, 12 mmol) was added to a solution of the mixture containing N-(2-t-butoxycarbonylaminophenyl)-4-(3-dimethylaminopropylaminomethyl)benzamide (Reference Compound No. 4-5, 10 g, 24 mmol) in DMSO (30 mL), and then the reaction mixture was stirred at room temperature for 15 hours. Water (300 mL) was added thereto, the whole was extracted with ethyl acetate (250 mL) twice, and then the organic layer was washed with brine (250 mL) twice. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform-methanol) to give 1.1 g of the title reference compound as a white amorphous product. (Yield 15%)

Workup

  1. addition5-1, 3.7 g, 12 mmol) was added to a solution of the mixture
  2. extractionthe whole was extracted with ethyl acetate (250 mL) twice
  3. washthe organic layer was washed with brine (250 mL) twice
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform-methanol)
  7. customto give 1.1 g of the title reference compound as a white amorphous product

Sources & evidence

ORD record
ord-d9b8cebf24fb4aa8ae0120faec79cd0b
Source dataset
uspto-grants-2011_12
Patent number
US08076332B2

Reaction notes

Loading…