Diisopropylethylamine → HCID 86692073, compound

HRID 509262Notes

Reaction equation

HRID 509262 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][CH:3]=1.Cl.O.[NH:13]1[CH2:18][CH2:17][C:16](=[O:19])[CH2:15][CH2:14]1.C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(#N)C.CO>[Br:1][C:2]1[N:7]=[C:6]([C:8]([N:13]2[CH2:18][CH2:17][C:16](=[O:19])[CH2:15][CH2:14]2)=[O:10])[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5939196-Bromopyridine-2-carboxylic acidHCID 2723901PiperonylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 86692073HCID 86692073, compoundYield 89.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

After 6-bromopicolinic acid (600 mg, 2.97 mmol) was suspended in acetonitrile (25 ml), 4-piperidone monohydrate hydrochloride (500 mg, 3.27 mmol), N,N-diisopropylethylamine (1 ml, 7.43 mmol), and HBTU (1.1 g, 3.56 mmol) were sequentially added thereto, and then the resulting mixture was stirred at room temperature under nitrogen stream for 13 hours. The resulting reaction liquid was concentrated under reduced pressure, followed by addition of MC (50 ml), and then washed with distilled water. The organic layer was dried over anhydrous magnesium sulfate, followed by filtration and concentration, and then the residue thus obtained was subjected to MPLC (3% MeOH/MC), to obtain 752 mg of yellow solid (89%).

Workup

  1. customThe resulting reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. additionfollowed by addition of MC (50 ml)
  4. washwashed with distilled water
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfollowed by filtration and concentration
  7. customthe residue thus obtained

Sources & evidence

ORD record
ord-0734bcb559474dc09fbfe2862ea0f54a
Source dataset
uspto-grants-2015_08
Patent number
US09096571B2

Reaction notes

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