Trifluoroacetic acid → 3-methyl-N-(4-{[2-(1H-pyrrol-2-yl)pyridin-4-yl]oxy}phenyl)-2-furamide

HRID 521782Notes

Reaction equation

HRID 521782 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7]([OH:9])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:34][C:35]1[CH:59]=[CH:58][C:38]([O:39][C:40]2[CH:45]=[CH:44][N:43]=[C:42]([C:46]3[N:47](C(OC(C)(C)C)=O)[CH:48]=[CH:49][CH:50]=3)[CH:41]=2)=[CH:37][CH:36]=1.C(N(CC)C(C)C)(C)C.FC(F)(F)C(O)=O>CN(C=O)C.C(Cl)Cl.O>[CH3:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7]([NH:34][C:35]1[CH:36]=[CH:37][C:38]([O:39][C:40]2[CH:45]=[CH:44][N:43]=[C:42]([C:46]3[NH:47][CH:48]=[CH:49][CH:50]=3)[CH:41]=2)=[CH:58][CH:59]=1)=[O:9]

Participants

9

Reactant 5

HCID 6422Trifluoroacetic acidHCID 781273-Methyl-2-furoic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58167895tert-butyl 2-[4-(4-aminophenoxy)pyridin-2-yl]-1H-pyrrole-1-carboxylate

Product 1

HCID 670425593-methyl-N-(4-{[2-(1H-pyrrol-2-yl)pyridin-4-yl]oxy}phenyl)-2-furamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 3-methyl-2-furoic acid (70 mg, 0.55 mmol), HATU (243 mg, 0.64 mmol), tert-butyl 2-[4-(4-aminophenoxyl)pyridin-2-yl]-1H-pyrrole-1-carboxylate (160 mg, 0.46 mmol) and N,N-diisopropylethylamine (148 mg, 1.15 mmol) in anhydrous DMF (10 ml) was stirred at 45° C. for 2 hours. The mixture was poured into 100 ml of water. The precipitates were filtered, washed with water and dried in vacuo to give the crude, which was dissolved in 5 ml of methylene chloride, followed by addition of trifluoroacetic acid (3 ml). The mixture was stirred at room temperature for 16 hours. The solvents were evaporated under reduced pressure. The residue was purified by reversed-phase chromatography with a gradient of 10˜50% acetonitrile/water to give 3-methyl-N-(4-{[2-(1H-pyrrol-2-yl)pyridin-4-yl]oxy}phenyl)-2-furamide as white solid. Yield: 56 mg, 34%.

Workup

  1. filtrationThe precipitates were filtered
  2. washwashed with water
  3. customdried in vacuo
  4. customto give the crude, which
  5. stirringThe mixture was stirred at room temperature for 16 hours
  6. customThe solvents were evaporated under reduced pressure
  7. customThe residue was purified by reversed-phase chromatography with a gradient of 10˜50% acetonitrile/water

Sources & evidence

ORD record
ord-bef90fb83daf44a6831c4bb3c88c8590
Source dataset
uspto-grants-2016_05
Patent number
US09328103B2

Reaction notes

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