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3-Hydroxyanthranilic Acid → N-(4-(trifluoromethyl)-2-(piperidin-1-yl)benzyl)-2-amino-3-hydroxybenzamide

HRID 1505206
Notes
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Reaction equation

HRID 1505206 reaction equation
[NH2:1][C:2]1[C:10]([OH:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.CCN=C=NCCCN(C)C.OC1C2N=NNC=2C=CC=1.[F:33][C:34]([F:50])([F:49])[C:35]1[CH:40]=[CH:39][C:38]([CH2:41][NH2:42])=[C:37]([N:43]2[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]2)[CH:36]=1>CN(C=O)C>[F:49][C:34]([F:33])([F:50])[C:35]1[CH:40]=[CH:39][C:38]([CH2:41][NH:42][C:4](=[O:6])[C:3]2[CH:7]=[CH:8][CH:9]=[C:10]([OH:11])[C:2]=2[NH2:1])=[C:37]([N:43]2[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]2)[CH:36]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 863-Hydroxyanthranilic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 58873623(4-(Trifluoromethyl)-2-(piperidin-1-yl)phenyl)-methanamineHCID 178418300HCID 178418300, compound

Product 1

HCID 67425570N-(4-(trifluoromethyl)-2-(piperidin-1-yl)benzyl)-2-amino-3-hydroxybenzamideYield 62.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-amino-3-hydroxybenzoic acid (1 g, 6.5 mmol) was dissolved in 20 ml of DMF and at 0° C. EDCI (1.4 g, 1.2 equiv.), hydroxybenzotriazole (1 g, 1.2 equiv.) and amine 2c (2 g, 1.2 equiv.) were added. The mixture was stirred at rt for 20 hours. The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1×20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by crystallization from EtOAc/ether gave 1.6 g of a beige solid. Yield=62.5% [M+1] 393.4 (C20H22F3N3O2 requires 393.4).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe crude was dissolved in AcOEt (30 ml)
  3. washwashed with water (1×20 ml) and brine
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe purification of the crude residue
  7. customby crystallization from EtOAc/ether

Sources & evidence

ORD record
ord-eae62ad99fe744e8a36f2cfd46153d6e
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09216975B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes