Triethylamine → HCID 58387908, compound

HRID 2080031Notes

Reaction equation

HRID 2080031 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.[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>ClCCl>[CH2:14]([O:21][C:22]1[CH:23]=[CH:24][C:25]([NH:28][C:11]([C:7]2[CH:6]=[C:5]3[C:10](=[CH:9][CH:8]=2)[N:1]=[CH:2][CH:3]=[CH:4]3)=[O:13])=[CH:26][CH:27]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 228604-BenzyloxyanilineHCID 825716-Quinolinecarboxylic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

Product 1

HCID 58387908HCID 58387908, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-quinolinecarboxylic acid (500 mg, 2.89 mmol) and 4-benzyloxyphenylamine (681 mg, 2.89 mmol) in dichloromethane (25 mL) were added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (1.53 g, 3.47 mmol) and triethylamine (0.96 mL, 6.94 mmol), and the solution was stirred overnight at room temperature. The solvent was evaporated, the residue was purified by NH silica gel column chromatography (hexane:ethyl acetate), and the title compound (194 mg, 19%) was obtained as a white solid.

Workup

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

Sources & evidence

ORD record
ord-a8649fd78382405b9a5bee0232a1f7b5
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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