Trifluoroacetic acid → Quinoxaline-6-carboxylic acid 3-phenoxybenzylamide

HRID 2080250Notes

Reaction equation

HRID 2080250 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([OH:13])=O)=[CH:8][CH:9]=2)[N:4]=[CH:3][CH:2]=1.[O:14]([C:21]1[CH:28]=[CH:27][C:24](CN)=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[N:29]1C=CC=C[C:30]=1OCC1C=CC(CNC(C2C(N)=NC(N)=CN=2)=O)=CC=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.C(N(CC)CC)C.FC(F)(F)C(O)=O>CN(C)C=O>[O:14]([C:15]1[CH:16]=[C:17]([CH:18]=[CH:19][CH:20]=1)[CH2:30][NH:29][C:11]([C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:1]=[CH:2][CH:3]=[N:4]2)=[O:13])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:27][CH:28]=1

Participants

8

Reactant 6

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 674813Quinoxaline-6-carboxylic acidHCID 2724699PyBOPHCID 2760343(4-Phenoxyphenyl)methanamineHCID 58875320HCID 58875320, compound

Product 1

HCID 58387890Quinoxaline-6-carboxylic acid 3-phenoxybenzylamideYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of quinoxaline-6-carboxylic acid described in Preparation Example I-1 (15 mg, 0.063 mmol) and 4-phenoxybenzylamine described in Preparation Example 3 (13 mg, 0.063 mmol) in N,N-dimethylformamide (2 mL) were added benzotriazol-1-yloxytris(pyrrolidino)phosphonium hexafluorophosphate (36 mg, 0.069 mmol) and triethylamine (19 μl, 0.14 mmol), which was then stirred at room temperature for 24 hours. The reaction mixture was concentrated, the residue was purified by reverse phase high performance liquid chromatography (acetonitrile-water mobile phase (containing 0.1% trifluoroacetic acid) was used), and the title compound (12 mg, 0.025 mmol, 40%) was obtained as a trifluoroacetic acid salt.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by reverse phase high performance liquid chromatography (acetonitrile-water mobile phase (containing 0.1% trifluoroacetic acid) was used)

Sources & evidence

ORD record
ord-c97b1c525ab94f2989d87a0777c7da3e
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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