Hydrochloric Acid → HCID 22144644, compound

HRID 1824978Notes

Reaction equation

HRID 1824978 reaction equation
[F:1][C:2]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([N+:14]([O-:16])=[O:15])=[CH:11][CH:12]=2)[CH:7]=[C:6]1[C:17](O)=[O:18].CN(C)CCCN=C=NCC.Cl.[F:37][C:38]1[CH:44]=[CH:43][C:41]([NH2:42])=[CH:40][CH:39]=1>CN(C)C1C=CN=CC=1.ClCCl.CN(C=O)C>[F:1][C:2]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([N+:14]([O-:16])=[O:15])=[CH:11][CH:12]=2)[CH:7]=[C:6]1[C:17]([NH:42][C:41]1[CH:43]=[CH:44][C:38]([F:37])=[CH:39][CH:40]=1)=[O:18]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 97314-FluoroanilineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 221446261-(2,4-difluorobenzyl)-5-nitro-1H-indole-2-carboxylic acid

Product 1

HCID 22144644HCID 22144644, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

389 mg (1.17 mmol) of 1-(2,4-difluorobenzyl)-5-nitro-1H-indole-2-carboxylic acid from Example XXII, 336 mg (1.76 mmol) of N′-(3-dimethylaminopropyl)-N-ethyl-carbodiimide×HCl and 71.5 mg (0.59 mmol) of 4-dimethylaminopyridine are initially charged in 30 ml of a 10:1 dichloromethane:DMF mixture. 156 mg (0.13 ml, 1.40 mmol) of 4-fluoroaniline are added, and the mixture is stirred at RT for 4 hours. For work-up the mixture is diluted and extracted with aqueous hydrochloric acid and ethyl acetate. The organic phase is washed with sat. sodium chloride solution, dried with sodium sulphate, filtered and dried under reduced pressure.

Workup

  1. additionFor work-up the mixture is diluted
  2. extractionextracted with aqueous hydrochloric acid and ethyl acetate
  3. washThe organic phase is washed with sat. sodium chloride solution
  4. dry with materialdried with sodium sulphate
  5. filtrationfiltered
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-4ec4e65a7c4742b3ad3eb4f684c08bfd
Source dataset
uspto-grants-2006_05
Patent number
US07045544B2

Reaction notes

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