Triethylamine → HCID 58875343, compound

HRID 2080231Notes

Reaction equation

HRID 2080231 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:7][CH:8]=1.[N:17]1[C:26]2[C:21](=[CH:22][C:23]([C:27](O)=[O:28])=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1.F[P-](F)(F)(F)(F)F.N1([P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O.O>[CH2:10]([NH:9][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[CH2:2][NH:1][C:27]([C:23]1[CH:22]=[C:21]2[C:26](=[CH:25][CH:24]=1)[N:17]=[CH:18][CH:19]=[CH:20]2)=[O:28])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 825716-Quinolinecarboxylic acidHCID 10938826Benzotriazol-1-yltris(dimethylamino)phosphonium hexafluorophosphateHCID 23130368HCID 23130368, compound

Product 1

HCID 58875343HCID 58875343, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(3-Aminomethyl-phenyl)-benzylamine (62 mg, 0.29 mmol), quinoline-6-carboxylic acid (52 mg, 0.30 mmol), benzotriazol-1-yl-tris(dimethylamino)phosphonium hexafluorophosphate (182 mg, 0.41 mmol) and triethylamine (114 μl, 0.81 mmol) were dissolved in N,N-dimethylformamide (0.5 mL), and the solution was stirred at room temperature for 2 hours. Water was added to the reaction solution, which was then extracted with ethyl acetate, the organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, the residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=1:1), and the title compound (73 mg, 0.198 mmol, 73%) was obtained as a white solid.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washthe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-01e3dd559cfd43e0ba2fc8c62862676f
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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