Dimethylformamide → HCID 59676891, compound

HRID 2104374Notes

Reaction equation

HRID 2104374 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=O)=[CH:5]2.O[N:15]1[C:19]2[CH:20]=CC=[CH:23][C:18]=2[N:17]=N1.Cl.CN(C)CCCN=C=NCC.CN(C)C=[O:39]>>[NH2:17][C@@H:18]1[CH2:23][O:39][CH2:20][C@@H:19]1[NH:15][C:11]([C:6]1[NH:7][C:8]2[C:4]([CH:5]=1)=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2)=[O:13]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 59676891HCID 59676891, compound

Conditions

Temperature
50 °C

Procedure

To a solution of the compound obtained in Referential Example 171 (0.5 g) in N,N-dimethylformamide (10 mL) were sequentially added 5-chloroindole-2-carboxylic acid (0.29 g), 1-hydroxybenzotriazole (0.2 g), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.6 g) at room temperature, followed by stirring at 50° C. for 1 day. The reaction mixture was concentrated, and the residue was diluted with a solvent mixture comprising chloroform and methanol (9:1). The diluted mixture was washed with saturated aqueous sodium hydrogencarbonate and saturated brine, and the organic layer was dried over sodium sulfate anhydrate. The solvent was distilled away under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform:methanol=95:5), to thereby give the title compound (0.2 g).

Workup

  1. customat room temperature
  2. concentrationThe reaction mixture was concentrated
  3. additionthe residue was diluted with a solvent mixture
  4. washThe diluted mixture was washed with saturated aqueous sodium hydrogencarbonate and saturated brine
  5. dry with materialthe organic layer was dried over sodium sulfate anhydrate
  6. distillationThe solvent was distilled away under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (chloroform:methanol=95:5)

Sources & evidence

ORD record
ord-df380673683645628f652aaf9db79f87
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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