Sodium Hydroxide → HCID 9868756, compound

HRID 1634135Notes

Reaction equation

HRID 1634135 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][C:6]([C:12]1[CH:20]=[CH:19][C:15]([C:16](O)=[O:17])=[CH:14][CH:13]=1)=[CH:5]2.CCN=C=NCCCN(C)C.C1C=NC2N(O)N=NC=2C=1.[NH2:42][CH:43]1[CH2:48][C:47]([CH3:50])([CH3:49])[N:46]([CH3:51])[C:45]([CH3:53])([CH3:52])[CH2:44]1.CCN(C(C)C)C(C)C.[OH-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][C:6]([C:12]1[CH:20]=[CH:19][C:15]([C:16]([NH:42][CH:43]3[CH2:44][C:45]([CH3:52])([CH3:53])[N:46]([CH3:51])[C:47]([CH3:50])([CH3:49])[CH2:48]3)=[O:17])=[CH:14][CH:13]=1)=[CH:5]2

Participants

8

Reactant 6

HCID 14798Sodium HydroxideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 6937924-Amino-1,2,2,6,6-pentamethylpiperidineHCID 10892106HCID 10892106, compound

Product 1

HCID 9868756HCID 9868756, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of) of 4-(5,6-dichloro-1H-indol-2-yl) benzoic acid (0.25 g, 0.82 mmol), WSC (0.156 g, 0.82 mmol), HOAT (0.11 g, 0.82 mmol), 4-amino-1,2,2,6,6-pentamethylpiperidine (0.209 g, 1.2 mmol), DIEA (0.212 g, 1.2 mmol) in DMF (3 ml) was stirred at room temperature for 16 h. The mixture was then poured on water, made basic by NaOH N and extracted with ethyl acetate. The organic solution was washed with water, dried over MgSO4, concentrated in vacuo, and the residue was purified by column chromatography (SiO2, CH2Cl2/CH3OH/NH4OH; 9/1/0.1), affording 0.35 g (0.76 mmol, yield 93%) of the title compound as white crystals, mp=325° C.

Workup

  1. additionThe mixture was then poured on water
  2. extractionextracted with ethyl acetate
  3. washThe organic solution was washed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customthe residue was purified by column chromatography (SiO2, CH2Cl2/CH3OH/NH4OH; 9/1/0.1)

Sources & evidence

ORD record
ord-a13bd16ec74842809f9c08a1771bf8e5
Source dataset
uspto-grants-2003_01
Patent number
US06506758B2

Reaction notes

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