Dimethylformamide → HCID 22405133, compound

HRID 441253Notes

Reaction equation

HRID 441253 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10](O)=[O:11])=[CH:4][CH:3]=1.[C:17](Cl)(=O)[C:18](Cl)=O.CN(C)[CH:25]=[O:26].[NH2:28][C:29]1[CH:56]=[CH:55][C:32]([C:33]([N:35]2[C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=3[N:39]([C:46](=[O:54])[C:47]3[CH:52]=[CH:51][C:50]([NH2:53])=[CH:49][CH:48]=3)[CH2:38][CH2:37][CH2:36]2)=[O:34])=[CH:31][CH:30]=1>ClCCl.C(Cl)(Cl)Cl.CO.C(N(CC)CC)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:18]2[CH:17]=[CH:16][CH:8]=[CH:9][C:10]=2[C:25]([NH:53][C:50]2[CH:51]=[CH:52][C:47]([C:46]([N:39]3[C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=4[N:35]([C:33](=[O:34])[C:32]4[CH:31]=[CH:30][C:29]([NH:28][C:10](=[O:11])[C:9]5[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=5[C:5]5[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=5)=[CH:56][CH:55]=4)[CH2:36][CH2:37][CH2:38]3)=[O:54])=[CH:48][CH:49]=2)=[O:26])=[CH:6][CH:7]=1

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 815682-(4-Methylphenyl)benzoic acidHCID 22405050HCID 22405050, compound

Product 1

HCID 22405133HCID 22405133, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a solution of 2-(4-methylphenyl)benzoic acid (240 mg) in dichloromethane (5 ml) was added oxalyl chloride (0.2 ml) and a few drop of N,N-dimethylformamide and the solution was stirred at 0° C. for 30 minutes. Dichloromethane was evaporated in vacuo to give a crude acid chloride as an oil. The crude acid chloride was added to a mixture of 1,5-bis(4-aminobenzoyl)-2,3,4,5-tetrhydro-1H-1,5-benzodiazepine (218 mg) and triethylamine (171 mg) in dichloromethane (5 ml) at 0° C. The mixture was stirred at ambient temperature for 18 hours, and then the resulting mixture was washed successively with 0.5N hydrochloric acid and saturated aqueous sodium bicarbonate solution. Drying, filtering and the removal of solvents afford a crude product. The crude product was subjected to silica gel column (eluent: 1% methanol in chloroform) to give 1,5-bis(4-[2-(4-methylphenyl)benzoylamino]-benzoyl}-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine (300 mg) as a white powder.

Workup

  1. customDichloromethane was evaporated in vacuo
  2. customto give a crude acid chloride as an oil
  3. washthe resulting mixture was washed successively with 0.5N hydrochloric acid and saturated aqueous sodium bicarbonate solution
  4. customDrying
  5. filtrationfiltering
  6. customthe removal of solvents
  7. customafford a crude product

Sources & evidence

ORD record
ord-b4a3ecbb87a34c1f8a1f61f6741cb993
Source dataset
uspto-grants-1996_05
Patent number
US05521170

Reaction notes

Loading…