Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 58368653, compound

HRID 1192565Notes

Reaction equation

HRID 1192565 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([C:20](O)=[O:21])=[CH:10][C:11]([CH:18]=[CH2:19])=[C:12]3[C:17]=2[N:16]=[CH:15][CH:14]=[CH:13]3)[CH:5]=[CH:6][CH:7]=1.Cl.[CH3:24][NH:25][O:26][CH3:27].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)C(C)C)(C)C>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([C:20]([N:25]([O:26][CH3:27])[CH3:24])=[O:21])=[CH:10][C:11]([CH:18]=[CH2:19])=[C:12]3[C:17]=2[N:16]=[CH:15][CH:14]=[CH:13]3)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 58368420HCID 58368420, compound

Product 1

HCID 58368653HCID 58368653, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 8-(3-fluorophenyl)-5-vinylquinoline-7-carboxylic acid (66 mg, 0.22 mmol), N,O-dimethylhydroxylamine hydrochloride (32.9 mg, 0.338 mmol) in N,N-dimethylformamide (0.4 mL) was added benzotriazol-1-yloxytris(dimethylamino) phosphonium hexafluorophosphate (0.149 g, 0.338 mmol). After stirring at room temperature for 30 minutes, N,N-diisopropylethylamine (0.118 mL, 0.675 mmol) was added to the resulting mixture. The reaction was stirred at room temperature overnight, quenched with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated to dryness under reduced pressure. The resdiue was purified on silica gel, eluting 0 to 50% ethyl acetate in hexane, to give the desired product (32 mg, 42%). LCMS calculated for C20H18FN2O2 (M+H)+: m/z=337.1; Found: 337.1.

Workup

  1. stirringThe reaction was stirred at room temperature overnight
  2. customquenched with water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated to dryness under reduced pressure
  7. customThe resdiue was purified on silica gel
  8. washeluting 0 to 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-c5b8802f0bf342ceb8e6801a54bd5340
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

Loading…