Salicylic Acid → HCID 67175546, compound

HRID 85358Notes

Reaction equation

HRID 85358 reaction equation
[N:1]1([C:7](=[O:29])[CH2:8][CH2:9][CH:10]=[CH:11][CH2:12][CH:13]=[CH:14][CH2:15][CH:16]=[CH:17][CH2:18][CH:19]=[CH:20][CH2:21][CH:22]=[CH:23][CH2:24][CH:25]=[CH:26][CH2:27][CH3:28])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:30](O)(=[O:38])[C:31]1[C:32](=[CH:34][CH:35]=[CH:36][CH:37]=1)[OH:33].CCN(CC)CC.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CC#N>[OH:33][C:32]1[CH:34]=[CH:35][CH:36]=[CH:37][C:31]=1[C:30]([N:4]1[CH2:5][CH2:6][N:1]([C:7](=[O:29])[CH2:8][CH2:9][CH:10]=[CH:11][CH2:12][CH:13]=[CH:14][CH2:15][CH:16]=[CH:17][CH2:18][CH:19]=[CH:20][CH2:21][CH:22]=[CH:23][CH2:24][CH:25]=[CH:26][CH2:27][CH3:28])[CH2:2][CH2:3]1)=[O:38]

Participants

6

Reactant 4

HCID 338Salicylic AcidHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 54312597HCID 54312597, compound

Product 1

HCID 67175546HCID 67175546, compoundYield 19.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 1-(piperazin-1-yl)-docosa-4,7,10,13,16,19-hexaen-1-one (1.17 g, 2.95 mmol), salicylic acid (0.61 g, 4.43 mmol) and Et3N (0.89 g, 8.85 mmol) in CH3CN (10 mL) was added HATU (1.68 g, 4.43 mmol), and the mixture was stirred (RT, 16 h). The solvent was removed under reduced pressure and the residue was extracted with EtOAc (4×50 mL). The combined organic layers were washed successively with 1N HCl, water, 5% NaHCO3 and water, and dried over MgSO4. The solvent was removed under reduced pressure. Purification of the crude product by preparative HPLC afforded 1-(4-(2-hydroxybenzoyl)piperazin-1-yl)docosa-4,7,10,13,16,19-hexaen-1-one (300 mg, 19.6%) as a light yellow oil. Mass calculated for C33H44N2O3=516.71; found: [M+H]+517.6.

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionthe residue was extracted with EtOAc (4×50 mL)
  3. washThe combined organic layers were washed successively with 1N HCl, water, 5% NaHCO3 and water
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed under reduced pressure
  6. customPurification of the crude product by preparative HPLC

Sources & evidence

ORD record
ord-a9b717fc59314d0c87542cdc586d2f28
Source dataset
uspto-grants-2014_09
Patent number
US08846972B2

Reaction notes

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