Diisopropylethylamine → HCID 86692072, compound

HRID 509260Notes

Reaction equation

HRID 509260 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][CH:3]=1.[CH:11]1[CH:16]=[N:15][CH:14]=[C:13]([C@H:17]2[NH:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:12]=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>[Br:1][C:2]1[N:7]=[C:6]([C:8]([N:22]2[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]2[C:13]2[CH:14]=[N:15][CH:16]=[CH:11][CH:12]=2)=[O:10])[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 205586AnabasineHCID 5939196-Bromopyridine-2-carboxylic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 86692072HCID 86692072, compoundYield 26.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

After 6-bromopicolinic acid (565 mg, 2.80 mmol) was suspended in acetonitrile (25 ml), anabasine (499 mg, 3.07 mmol), N,N-diisopropylethylamine (0.73 ml, 4.20 mmol), and HBTU (1.27 g, 3.36 mmol) were sequentially added thereto, and then the resulting mixture was stirred at room temperature under nitrogen stream for 3 hours. The resulting reaction liquid was concentrated under reduced pressure, and then the residue thus obtained was subjected to MPLC (40% EtOAc/Hexanes), to obtain 255 mg of white solid (26%).

Workup

  1. customThe resulting reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. customthe residue thus obtained

Sources & evidence

ORD record
ord-ab50413c2ea146998fcd444b624742bc
Source dataset
uspto-grants-2015_08
Patent number
US09096571B2

Reaction notes

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