3-Hydroxyanthranilic Acid → HCID 67424503, compound

HRID 1505204Notes

Reaction equation

HRID 1505204 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:44])([F:43])[C:35]1[CH:42]=[CH:41][C:38]([CH2:39][NH2:40])=[CH:37][CH:36]=1>CN(C=O)C>[F:33][C:34]([F:43])([F:44])[C:35]1[CH:42]=[CH:41][C:38]([CH2:39][NH:40][C:4](=[O:6])[C:3]2[CH:7]=[CH:8][CH:9]=[C:10]([OH:11])[C:2]=2[NH2:1])=[CH:37][CH:36]=1

Participants

6

Reactant 4

HCID 863-Hydroxyanthranilic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 768044-(Trifluoromethyl)benzylamineHCID 178418300HCID 178418300, compound

Product 1

HCID 67424503HCID 67424503, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-amino-3-hydroxybenzoic acid (2 g, 13 mmol) was dissolved in 20 ml of DMF and at 0° C. EDCI (2.7 g, 1.2 equiv.), hydroxybenzotriazole (1.9 g, 1.2 equiv.) and 4-trifluoromethylbenzylamine (2 ml, 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 3.5 g of a beige solid. Yield=86% 1HNMR (DMSO, 200 MHz) δ 4.49 (2H, d, J=5.6 Hz), 6.00 (2H, bs), 6.41 (1H, t, J=8 Hz), 6.76 (1H, d, J=7.6 Hz), 7.11 (1H, d, J=8.2 Hz), 7.51 (2H, d, J=8 Hz), 7.69 (2H, d, J=8 Hz), 8.81 (1H, bt), 9.58 (1H, bs); [M+1] 311.1 (C15H13F3N2O2 requires 310.27).

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-5c306bdc4512481fb0bae4328f029caf
Source dataset
uspto-grants-2015_12
Patent number
US09216975B2

Reaction notes

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