Trifluoroacetic acid → Methyl 2-[3-(4-fluoro-3-thiophen-2-ylphenyl)ureido]-2-methylpropionate

HRID 2356696Notes

Reaction equation

HRID 2356696 reaction equation
FC(F)(F)[C:3]([OH:5])=O.[F:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][C:10]=1[C:16]1[S:17][CH:18]=[CH:19][CH:20]=1.C([N:23](CC)CC)C.N([CH2:31][CH:32]([CH3:37])[C:33]([O:35][CH3:36])=[O:34])=C=O>O1CCCC1>[F:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:3](=[O:5])[NH:23][C:32]([CH3:31])([CH3:37])[C:33]([O:35][CH3:36])=[O:34])=[CH:11][C:10]=1[C:16]1[S:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 13063727Methyl 3-isocyanato-2-methylpropanoateHCID 578293344-Fluoro-3-(thiophen-2-yl)aniline

Product 1

HCID 57829328Methyl 2-[3-(4-fluoro-3-thiophen-2-ylphenyl)ureido]-2-methylpropionate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

According to process “A′”, 0.12 g of the trifluoroacetic acid salt of compound 267.4 was dissolved at room temperature in 5 ml of dry tetrahydrofuran, admixed with 0.17 ml of triethylamine and then admixed dropwise with a solution of 0.10 g of methyl isocyanatomethylpropionate in 2 ml of dry tetrahydrofuran. The mixture was stirred at room temperature for 2 hours. For workup, the mixture was concentrated under reduced pressure, and the residue was stirred with water, filtered, washed with water and dried. Methyl 2-[3-(4-fluoro-3-thiophen-2-ylphenyl)ureido]-2-methylpropionate (267.3) was obtained. Molecular weight 336.39 (C16H17FN2O3S); retention time Rt=1.46 min. [F]; MS (ESI): 337.05 (MH+).

Workup

  1. concentrationFor workup, the mixture was concentrated under reduced pressure
  2. stirringthe residue was stirred with water
  3. filtrationfiltered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-1116b2eebb9949b598d40de9eade8f96
Source dataset
uspto-grants-2010_07
Patent number
US07759366B2

Reaction notes

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