Triethylamine → 3-{4-[3-(5-tertbutyl-2-p-tolyl-2H-pyrazol-3-yl)ureido]phenyl}-1H-indole-2-carboxamide

HRID 230553Notes

Reaction equation

HRID 230553 reaction equation
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.[NH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[NH:29][C:28]=2[C:36]([NH2:38])=[O:37])=[CH:23][CH:22]=1.[C:39]([C:43]1[CH:44]=[C:45]([NH2:55])[N:46]([C:48]2[CH:53]=[CH:52][C:51]([CH3:54])=[CH:50][CH:49]=2)[N:47]=1)([CH3:42])([CH3:41])[CH3:40]>O1CCCC1>[C:39]([C:43]1[CH:44]=[C:45]([NH:55][C:5](=[O:11])[NH:20][C:21]2[CH:22]=[CH:23][C:24]([C:27]3[C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[NH:29][C:28]=3[C:36]([NH2:38])=[O:37])=[CH:25][CH:26]=2)[N:46]([C:48]2[CH:49]=[CH:50][C:51]([CH3:54])=[CH:52][CH:53]=2)[N:47]=1)([CH3:42])([CH3:41])[CH3:40]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 29741323-tert-butyl-1-(4-methylphenyl)-1H-pyrazol-5-amineHCID 577628333-(4-Aminophenyl)-1H-indole-2-carboxamide

Product 1

HCID 115552333-{4-[3-(5-tertbutyl-2-p-tolyl-2H-pyrazol-3-yl)ureido]phenyl}-1H-indole-2-carboxamideYield 204.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

43 mg of triphosgene followed by 110 μl of triethylamine at 0° C. are added to a solution of 100 mg of 3-(4-aminophenyl)-1H-indole-2-carboxamide (example 1) in 18 ml of tetrahydrofuran. The mixture is stirred for one hour at ambient temperature and then 110 mg of 5-tert-butyl-2-p-tolyl-2H-pyrazol-3-ylamine are added. The mixture is stirred for one hour and concentrated under reduced pressure, and the residue is triturated with 2 ml of ethyl acetate, to give a white solid. After filtration and drying, 150 mg of 3-{4-[3-(5-tertbutyl-2-p-tolyl-2H-pyrazol-3-yl)ureido]phenyl}-1H-indole-2-carboxamide are obtained, the characteristics of which are as follows:

Workup

  1. stirringThe mixture is stirred for one hour
  2. concentrationconcentrated under reduced pressure
  3. customthe residue is triturated with 2 ml of ethyl acetate
  4. customto give a white solid
  5. filtrationAfter filtration
  6. customdrying

Sources & evidence

ORD record
ord-1accc1a177e347c69da15df7b1b259c9
Source dataset
uspto-grants-2009_07
Patent number
US07566736B2

Reaction notes

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