3-Methyl-2-furoic acid → HCID 51001780, compound

HRID 1915061Notes

Reaction equation

HRID 1915061 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=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[NH:43]1[CH:47]=[CH:46][CH:45]=[C:44]1[C:48]1[CH:53]=[C:52]([O:54][C:55]2[CH:56]=[C:57]([CH:59]=[CH:60][CH:61]=2)[NH2:58])[CH:51]=[CH:50][N:49]=1>CN(C=O)C.O>[CH3:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7]([NH:58][C:57]1[CH:59]=[CH:60][CH:61]=[C:55]([O:54][C:52]2[CH:51]=[CH:50][N:49]=[C:48]([C:44]3[NH:43][CH:47]=[CH:46][CH:45]=3)[CH:53]=2)[CH:56]=1)=[O:9]

Participants

7

Reactant 4

HCID 781273-Methyl-2-furoic acidHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69810816HCID 69810816, compound

Product 1

HCID 51001780HCID 51001780, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-methyl-2-furoic acid (60 mg, 0.48 mmol), HBTU (198 mg, 0.52 mmol) and N,N-diisopropylethylamine (129 mg, 1.0 mmol) in anhydrous DMF (10 ml) was stirred at room temperature for 10 minutes, followed by addition of 3-{[2-(1H-pyrrol-2-yl)pyridin-4-yl]oxy}aniline (100 mg, 0.40 mmol). The mixture was stirred at 70° C. for 3 hours and poured into 100 ml of water. The precipitates were filtered, washed with water and dried in vacuo to give the crude, which was purified by silica gel chromatography eluting with 3-5% MeOH/CHCl3 to give 3-methyl-N-(3-{[2-(1H-pyrrol-2-yl)pyridin-4-yl]oxy}phenyl)-2-furamide as white solid. Yield: 52 mg, 36%.

Workup

  1. stirringThe mixture was stirred at 70° C. for 3 hours
  2. filtrationThe precipitates were filtered
  3. washwashed with water
  4. customdried in vacuo
  5. customto give the crude, which
  6. customwas purified by silica gel chromatography
  7. washeluting with 3-5% MeOH/CHCl3

Sources & evidence

ORD record
ord-7a6e68eab19f4081806577b0e24a45a2
Source dataset
uspto-grants-2013_12
Patent number
US08614234B2

Reaction notes

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