Diisopropylethylamine → HCID 67042755, compound

HRID 521809Notes

Reaction equation

HRID 521809 reaction equation
OC(C(F)(F)F)=O.[NH:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13]1[CH:18]=[C:17]([C:19]2[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=2)[CH:16]=[CH:15][N:14]=1.[F:26][C:27]1[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][C:28]=1[N:34]=[C:35]=[O:36].C(N(CC)C(C)C)(C)C>C1COCC1>[F:26][C:27]1[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][C:28]=1[NH:34][C:35]([NH:23][C:22]1[CH:24]=[CH:25][C:19]([C:17]2[CH:16]=[CH:15][N:14]=[C:13]([C:9]3[NH:8][CH:12]=[CH:11][CH:10]=3)[CH:18]=2)=[CH:20][CH:21]=1)=[O:36]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27333772-Fluoro-5-methylphenyl isocyanateHCID 86651559HCID 86651559, compound

Product 1

HCID 67042755HCID 67042755, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 4-(2-(1H-pyrrol-2-yl)pyridin-4-yl)aniline TFA salt (60 mg, 0.17 mmol) in anhydrous THF (10 ml) was added 2-fluoro-5-methyl-phenylisocyanate (48 mg, 0.32 mmol) and N,N-diisopropylethylamine (40 mg, 0.31 mmol). After 1 hour, the reaction mixture was evaporated and purified by silica gel chromatography with 2-3% MeOH/CHCl3 to give 1-(2-fluoro-5-methylphenyl)-3-{4-[2-(1H-pyrrol-2-yl)pyridin-4-yl]phenyl}urea as off-white solid. Yield: 28 mg.

Workup

  1. customthe reaction mixture was evaporated
  2. custompurified by silica gel chromatography with 2-3% MeOH/CHCl3

Sources & evidence

ORD record
ord-ffcb18de5c77491d8afb721ac0a95aca
Source dataset
uspto-grants-2016_05
Patent number
US09328103B2

Reaction notes

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