Triethylamine → HCID 71254937, compound

HRID 714491Notes

Reaction equation

HRID 714491 reaction equation
[OH:1][C@@H:2]1[CH2:11][C:10]2[C:5](=[CH:6][C:7]([O:14][CH3:15])=[CH:8][C:9]=2[O:12][CH3:13])[O:4][C@@H:3]1[C:16]1[CH:24]=[CH:23]C(C(O)=O)=[C:18]([O:25][CH3:26])[CH:17]=1.[CH2:27]([N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])[CH3:28].CN(C([O:41]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C[N:59]1[CH2:64]CNCC1>CN(C=O)C.C(OCC)(=O)C>[OH:1][C@@H:2]1[CH2:11][C:10]2[C:5](=[CH:6][C:7]([O:14][CH3:15])=[CH:8][C:9]=2[O:12][CH3:13])[O:4][C@@H:3]1[C:16]1[CH:24]=[CH:23][C:28]([C:27]([N:29]2[CH2:32][CH2:33][N:59]([CH3:64])[CH2:31][CH2:30]2)=[O:41])=[C:18]([O:25][CH3:26])[CH:17]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 71254842HCID 71254842, compound

Product 1

HCID 71254937HCID 71254937, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-((2R,3R)-3-hydroxy-5,7-dimethoxychroman-2-yl)-2-methoxybenzoic acid (20 mg, 0.08 mmol) and triethylamine (22 μL, 0.16 mmol) in DMF (1 mL) was added HATU (38 mg, 0.1 mmol). The mixture was stirred for 0.5 hr and N-methylpiperazine (20 μL, 0.16 mmol) was added and the reaction was stirred for 12 hr. The mixture was diluted with ethyl acetate, washed with sat. sodium carbonate and brine, dried over sodium sulfate, and concentrated. The crude product was purified by preparative reverse phase HPLC using a gradient of 5% to 30% acetonitrile/(0.2% formic acid/water) over 10 min, analyzing at 280 nm. The appropriate fractions were frozen and lyophilized to give (4-((2R,3R)-3-hydroxy-5,7-dimethoxychroman-2-yl)-2 methoxyphenyl)(4-methylpiperazin-1-yl)methanone.

Workup

  1. stirringthe reaction was stirred for 12 hr
  2. washwashed with sat. sodium carbonate and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe crude product was purified by preparative reverse phase HPLC
  6. customover 10 min
  7. temperatureThe appropriate fractions were frozen

Sources & evidence

ORD record
ord-693047bf0829425caf65aab4d01631eb
Source dataset
uspto-grants-2015_11
Patent number
US09187448B2

Reaction notes

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