Triethylamine → 3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-5-(2-oxo-tetrahydro-pyrimidin-1-ylmethyl)-benzamide

HRID 20779

Reaction equation

HRID 20779 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][CH2:6][C:7]1[C:8]([F:30])=[C:9]([F:29])[C:10]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=2[F:28])=[C:11]([CH:19]=1)[C:12]([NH:14][O:15][CH2:16][CH2:17][OH:18])=[O:13].C1C(=O)N(OC(ON2C(=O)CCC2=O)=O)[C:33](=[O:34])C1.C(N(CC)CC)C>C1COCC1.CC#N>[F:29][C:9]1[C:10]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=2[F:28])=[C:11]([CH:19]=[C:7]([CH2:6][N:5]2[CH2:4][CH2:3][CH2:2][NH:1][C:33]2=[O:34])[C:8]=1[F:30])[C:12]([NH:14][O:15][CH2:16][CH2:17][OH:18])=[O:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 676246Di(succinimido) carbonateHCID 593479915-[(3-amino-propylamino)-methyl]-3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-benzamide

Product 1

HCID 115704243,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-5-(2-oxo-tetrahydro-pyrimidin-1-ylmethyl)-benzamideYield 61.2%

Reagents, catalysts & solvents 1

HCID 22177404Acetonitrile tetrahydrofuranSolvent

Procedure

The amine synthesized in Step A (66.4 mg, 0.1233 mmol) was dissolved in THF:CH3CN (1:1 v/v, 3.0 ml). N,N-disuccinimidyl carbonate (47.4 mg, 1.5 eq., 0.1849 mmol) and triethylamine (103.1 μl, 6.0 eq., 0.7398 mmol) were added sequentially to this solution, and the mixture was stirred at room temperature for 20 hours. The solvent was removed under reduced pressure, and the residue was purified by LC/MS to give white crystals (42.6 mg).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by LC/MS

Sources & evidence

ORD record
ord-187687b8fb3d433684e8cd7fd4d0ba73
Source dataset
uspto-grants-2010_06
Patent number
US07745663B2

Linked notes

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