1,2-Dichloroethane → HCID 22144671, compound

HRID 1825011Notes

Reaction equation

HRID 1825011 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][C:9]([CH3:33])([CH3:32])[CH2:10][C:11]([NH:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[N:19]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:18]([C:29]([OH:31])=O)=[CH:17]2)=[O:12].C(Cl)CCl.Cl>CN(C1C=CN=CC=1)C.ClCCl>[CH3:33][C:9]([CH3:8])([CH3:32])[CH2:10][C:11]([NH:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[N:19]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:18]([C:29]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:31])=[CH:17]2)=[O:12]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 6115AnilineHCID 22144623HCID 22144623, compound

Product 1

HCID 22144671HCID 22144671, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

7.9 mg (0.09 mmol) of aniline are added to a solution of 27 mg (0.08 mmol) of 5-[(3,3-dimethylbutanoyl)amino]-1-phenyl-1H-indole-2-carboxylic acid (Example LIX), 4.7 mg (0.09 mmol) of DMAP and 22.2 mg (0.12 mmol) of EDC in 2 ml of dichloromethane, and the mixture is stirred at RT for 3 h. For work-up, 1-molar hydrochloric acid is added and the mixture is extracted repeatedly with dichloromethane. The combined organic phases are washed with saturated sodium bicarbonate solution and water, dried over sodium sulphate and filtered. Removal of the solvent under reduced pressure gives 35 mg (99% of theory) of the product.

Workup

  1. extractionthe mixture is extracted repeatedly with dichloromethane
  2. washThe combined organic phases are washed with saturated sodium bicarbonate solution and water
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customRemoval of the solvent under reduced pressure
  6. customgives 35 mg (99% of theory) of the product

Sources & evidence

ORD record
ord-f77ef65c48c14bf19f67f64e46b358cc
Source dataset
uspto-grants-2006_05
Patent number
US07045544B2

Reaction notes

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