Salicyluric Acid → HCID 25165129, compound

HRID 1178051Notes

Reaction equation

HRID 1178051 reaction equation
CCN(C(C)C)C(C)C.[OH:10][C:11]1[CH:23]=[CH:22][CH:21]=[CH:20][C:12]=1[C:13]([NH:15][CH2:16][C:17]([OH:19])=O)=[O:14].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[N:45]1([C:51]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=2[C:59]([F:62])([F:61])[F:60])=[O:52])[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]1>CN(C=O)C.O>[OH:10][C:11]1[CH:23]=[CH:22][CH:21]=[CH:20][C:12]=1[C:13]([NH:15][CH2:16][C:17](=[O:19])[N:48]1[CH2:49][CH2:50][N:45]([C:51](=[O:52])[C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=2[C:59]([F:62])([F:60])[F:61])[CH2:46][CH2:47]1)=[O:14]

Participants

8

Reactant 5

HCID 10253Salicyluric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 167337841-[2-(Trifluoromethyl)benzoyl]piperazine

Product 1

HCID 25165129HCID 25165129, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (0.239 mL, 1.39 mmol) was added drop wise to (2-hydroxy-benzoyl amino)-acetic acid (90 mg, 0.46 mmol) in DMF (7 mL). EDCI (221 mg, 1.15 mmol) and HOBT (74 mg, 0.55 mmol) were added consecutively and after 5 minutes, piperazin-1-yl-(2-trifluoromethyl-phenyl)-methanone (162 mg, 0.55 mmol) was added. The resulting mixture was stirred at room temperature overnight. Water was then added, and the product was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford the crude product. Purification using column chromatography (silica gel of mesh size of 60-120 using 70:30 EtOAc:hexane as eluent) afforded 2-hydroxy-N-[2-Oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazine-1-yl]-ethyl]-benzamide in 25% yield. LC-MS purity: 97%, 1H NMR (DMSO-D6): δ 12.0 (s, 1H), 9.1 (t, 1H), 7.9 (m, 3H), 7.7 (d, 1H), 7.6 (m, 1H), 7.4 (t, 1H), 6.9 (t, 2H), 4.2 (dd, 2H), 3.6 (m, 4H), 3.4 (m, 2H), 3.2 (m, 2H).

Workup

  1. extractionthe product was extracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto afford the crude product
  6. customPurification

Sources & evidence

ORD record
ord-73b9ddea9eea45e5832f8785a247663c
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

Loading…