1H-1,2,4-Triazole → HCID 25052173, compound

HRID 252612Notes

Reaction equation

HRID 252612 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH2:13][CH2:14][CH2:15]I)=[CH:9][CH:10]=2)[N:5]([CH:17]2[CH2:20][CH2:19][CH2:18]2)[C:4]=1[C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28]([NH:30][CH:31]([CH3:33])[CH3:32])=[O:29])=[CH:23][CH:22]=1)#[N:2].[NH:34]1[CH:38]=[N:37][CH:36]=[N:35]1.[Na]>CN(C=O)C>[C:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH2:13][CH2:14][CH2:15][N:34]3[CH:38]=[N:37][CH:36]=[N:35]3)=[CH:9][CH:10]=2)[N:5]([CH:17]2[CH2:20][CH2:19][CH2:18]2)[C:4]=1[C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28]([NH:30][CH:31]([CH3:33])[CH3:32])=[O:29])=[CH:23][CH:22]=1)#[N:2]

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 5360545SodiumHCID 59425553HCID 59425553, compound

Product 1

HCID 25052173HCID 25052173, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 1 mL of the DMF solution above, 1-{4-[3-cyano-1-cyclobutyl-6-(3-iodopropoxy)-1H-indol-2-yl]-phenyl}-3-isopropyl-urea (34 mg, 0.062 mmol) is added anhydrous 1,2,4-triazole, sodium salt (10.0 mg, 0.110 mmol). After stirring overnight at rt, the reaction mixture is filtered and purified by preparatory LC/UV purification. The solvent is removed to obtain 12.3 mg (40%) of 1-{4-[3-cyano-1-cyclobutyl-6-(3-[1,2,4]triazol-1-yl-propoxy)-1H-indol-2-yl]-phenyl}-3-isopropyl-urea (compound 1314), as a white powder.

Workup

  1. filtrationthe reaction mixture is filtered
  2. custompurified by preparatory LC/UV purification
  3. customThe solvent is removed

Sources & evidence

ORD record
ord-6d72cd7e9d944d34a7729276e2015fbe
Source dataset
uspto-grants-2011_01
Patent number
US07868037B2

Reaction notes

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