Triethylamine → HCID 58387963, compound

HRID 2079962Notes

Reaction equation

HRID 2079962 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.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:45][C:46]1[CH:47]=[C:48]([CH:57]=[CH:58][CH:59]=1)[CH2:49][N:50]1[CH:54]=[CH:53][C:52]([CH2:55][NH2:56])=[CH:51]1>CN(C)C=O.[Cl-].[Na+].O>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:56][CH2:55][C:52]2[CH:53]=[CH:54][N:50]([CH2:49][C:48]3[CH:57]=[CH:58][CH:59]=[C:46]([F:45])[CH:47]=3)[CH:51]=2)=[O:8])=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 792226-Chloronicotinic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 58387909HCID 58387909, compound

Product 1

HCID 58387963HCID 58387963, compoundYield 67.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

6-chloro-nicotinic acid (100 mg, 0.58 mmol), triethylamine (0.194 mL, 1.39 mmol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (308 mg, 0.696 mmol) were dissolved in N,N-dimethylformamide (3 mL), C-(1-(3-fluoro-benzyl)-1H-pyrrol-3-yl)-methylamine (142 mg, 0.695 mmol) described in Preparation Example 59 was added, and the solution was stirred for 15 hours 10 minutes at room temperature. After the reaction was completed, the reaction solution was poured into brine, and the solution was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, then the solution was concentrated, the resulting residue was purified by NH silica gel column chromatography (ethyl acetate:hexane=1:1), and the title compound (0.14 g, 0.39 mmol, 67%) was obtained.

Workup

  1. additionwas added
  2. extractionthe solution was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationthe solution was concentrated
  5. customthe resulting residue was purified by NH silica gel column chromatography (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-3974b6837e344f9c8a272a64dd5c412a
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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