Triethylamine → 2,6-Diamino-N-(5-(4-fluoro-phenoxy)-furan-2-ylmethyl)-nicotinamide

HRID 2080169Notes

Reaction equation

HRID 2080169 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[F:46][C:47]1[CH:60]=[CH:59][C:50]([O:51][C:52]2[O:56][C:55]([CH2:57][NH2:58])=[CH:54][CH:53]=2)=[CH:49][CH:48]=1>CN(C)C=O.[Cl-].[Na+].O>[NH2:1][C:2]1[N:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH:58][CH2:57][C:55]1[O:56][C:52]([O:51][C:50]2[CH:59]=[CH:60][C:47]([F:46])=[CH:48][CH:49]=2)=[CH:53][CH:54]=1)=[O:6]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 189772452,6-Diaminonicotinic acidHCID 23130578C-(5-(4-Fluoro-phenoxy)-furan-2-yl)methylamine

Product 1

HCID 231304652,6-Diamino-N-(5-(4-fluoro-phenoxy)-furan-2-ylmethyl)-nicotinamideYield 36%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

2,6-Diamino-nicotinic acid described in Preparation Example A-15 (0.15 g, 0.98 mmol), triethylamine (0.41 mL, 2.94 mmol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (0.65 g, 1.47 mmol) were dissolved in N,N-dimethylformamide (5 mL), and the solution was stirred at room temperature for 10 minutes. Then, a solution of C-(5-(4-fluoro-phenoxy)-furan-2-yl)methylamine described in Preparation Example 169 (304 mg, 1.47 mmol) in N,N-dimethylformamide (1 mL) was added thereto, followed by stirring at room temperature for 14 hours 50 minutes. After the reaction was completed, reaction solution was poured into brine, the solution was extracted with ethyl acetate, the fractionated organic layer was dried over anhydrous magnesium sulfate and then concentrated. The obtained residue was subjected to silica gel column chromatography, eluted with solvent (ethyl acetate), and the title compound (0.12 g, 0.35 mmol, 36%) was obtained.

Workup

  1. additionwas added
  2. stirringby stirring at room temperature for 14 hours 50 minutes
  3. customreaction solution
  4. extractionthe solution was extracted with ethyl acetate
  5. dry with materialthe fractionated organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. washeluted with solvent (ethyl acetate)

Sources & evidence

ORD record
ord-4d9dd0481b54444990869dc54ab02308
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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