Cyanuric chloride → HCID 57396254, compound

HRID 400696Notes

Reaction equation

HRID 400696 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:31][CH3:32])=[C:6]([C:8]([CH3:30])([CH3:29])[CH2:9][C:10]([OH:28])([C:24]([F:27])([F:26])[F:25])[CH2:11][C:12]2[NH:13][C:14]3[CH:15]=[CH:16][CH:17]=[C:18]([C:21]([NH2:23])=O)[C:19]=3[CH:20]=2)[CH:7]=1.N1C(Cl)=NC(Cl)=NC=1Cl.C(=O)(O)[O-].[Na+]>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:31][CH3:32])=[C:6]([C:8]([CH3:29])([CH3:30])[CH2:9][C:10]([OH:28])([C:24]([F:26])([F:27])[F:25])[CH2:11][C:12]2[NH:13][C:14]3[CH:15]=[CH:16][CH:17]=[C:18]([C:21]#[N:23])[C:19]=3[CH:20]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 7954Cyanuric chlorideHCID 516892Sodium BicarbonateHCID 60026288HCID 60026288, compound

Product 1

HCID 57396254HCID 57396254, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution 2-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1H-indole-4-carboxylic acid amide (95 mg, 0.21 mmol) in 1 mL of DMF was reacted with cyanuric chloride (46 mg, 0.25 mmol). After 3 hours, the mixture was treated with sodium bicarbonate, extracted with dichloromethane. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to give 33 mg of the title product as off-white solid (36% yield).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-838cb8ea3ecf42dabf5286b2eb5f39cc
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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