Triethylamine → HCID 58875359, compound

HRID 2080242Notes

Reaction equation

HRID 2080242 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([OH:13])=O)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH3:14][C:15]([CH3:27])=[CH:16][CH2:17][O:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22][NH2:23].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>O1CCCC1>[CH3:14][C:15]([CH3:27])=[CH:16][CH2:17][O:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22][NH:23][C:11]([C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:1]=[CH:2][CH:3]=[CH:4]2)=[O:13]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 825716-Quinolinecarboxylic acidHCID 10938826Benzotriazol-1-yltris(dimethylamino)phosphonium hexafluorophosphateHCID 23130698HCID 23130698, compound

Product 1

HCID 58875359HCID 58875359, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-Quinolinecarboxylic acid (100 mg, 0.577 mmol), 3-(3-methyl-2-butenyloxy)-benzylamine described in Preparation Example 134 (112 mg, 0.635 mmol), benzotriazol-1-yl-tris(dimethylamino)phosphonium hexafluorophosphate (306 mg, 0.693 mmol) and triethylamine (0.12 mL, 0.87 mmol) were dissolved in tetrahydrofuran (5 mL), and the solution was stirred at room temperature for 3 hours. The solvent was evaporated in vacuo, the obtained residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=4:1), and the title compound (153 mg, 80.1%) was obtained as a white solid.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe obtained residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-907c91df71f74ade99ea94693f772876
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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