Dimethylformamide → HCID 11802712, compound

HRID 2260062Notes

Reaction equation

HRID 2260062 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5]2[C:10]([CH2:11][CH3:12])=[C:9]([C:13]([OH:15])=[O:14])[N:8]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[C:29]4[NH:33][N:32]=[N:31][N:30]=4)=[CH:19][CH:18]=3)[N:6]2[N:7]=1)[CH3:2].CN(C)C=O.[C:39]1([C:45](Cl)([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C(N(CC)CC)C>[CH2:1]([C:3]1[N:4]=[C:5]2[C:10]([CH2:11][CH3:12])=[C:9]([C:13]([OH:15])=[O:14])[N:8]([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[C:29]4[N:30]([C:45]([C:39]5[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=5)([C:52]5[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=5)[C:46]5[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=5)[N:31]=[N:32][N:33]=4)=[CH:21][CH:22]=3)[N:6]2[N:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 6456Trityl chlorideHCID 178437447HCID 178437447, compound

Product 1

HCID 11802712HCID 11802712, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture consisting of 8.83 g of 2,7-diethyl-5-[[2'-(tetrazol-5-yl)biphenyl-4-yl]methyl]-5H-pyrazolo[1,5-b][1,2,4]triazole-6-carboxylic acid, 60 ml of N,N-dimethylformamide, 2.82 ml of triethylamine and 5.66 g of triphenylmethyl chloride was stirred overnight at room temperature. After removing the solvent by distillation under a reduced pressure, the thus obtained residue was mixed with 250 ml of ethyl acetate and then washed with 150 ml of water. Thereafter, the ethyl acetate layer was stirred overnight at room temperature, and the solid material thus precipitated was collected by filtration to give 6.98 g of 2,7-diethyl-5-[[2'-(N-triphenylmethyl-tetrazol-5-yl)biphenyl-4-yl]methyl]-5H-pyrazolo[1,5-b][1,2,4]triazole-6-carboxylic acid.

Workup

  1. customAfter removing the solvent
  2. distillationby distillation under a reduced pressure
  3. additionthe thus obtained residue was mixed with 250 ml of ethyl acetate
  4. washwashed with 150 ml of water
  5. stirringThereafter, the ethyl acetate layer was stirred overnight at room temperature
  6. customthe solid material thus precipitated
  7. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-3fce32f9b56743a7849274072921ef84
Source dataset
uspto-grants-1995_12
Patent number
US05475114

Reaction notes

Loading…