3-Methylsalicylic Acid → HCID 59314109, compound

HRID 1047679Notes

Reaction equation

HRID 1047679 reaction equation
[OH:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[CH3:12][O:13][C:14]([C:16]1([NH2:29])[CH2:27][C:26]2[C:28]3[C:22]([CH:23]=[CH:24][CH:25]=2)=[CH:21][CH:20]=[CH:19][C:18]=3[CH2:17]1)=[O:15].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:12][O:13][C:14]([C:16]1([NH:29][C:4](=[O:5])[C:3]2[CH:7]=[CH:8][CH:9]=[C:10]([CH3:11])[C:2]=2[OH:1])[CH2:27][C:26]2[C:28]3[C:22]([CH:23]=[CH:24][CH:25]=2)=[CH:21][CH:20]=[CH:19][C:18]=3[CH2:17]1)=[O:15]

Participants

6

Reactant 4

HCID 67383-Methylsalicylic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59314280HCID 59314280, compound

Product 1

HCID 59314109HCID 59314109, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-hydroxy-3-methyl-benzoic acid (1.12 g, 7.4 mmol), 2-amino-2,3-dihydro-1H-phenalene-2-carboxylic acid methyl ester (2.05 g, 7.4 mmol), HATU (3.38 g, 8.9 mmol) in anhydrous DMF (28 mL) is added DIPEA (4.89 mL, 29.6 mmol). The resulting solution is stirred at RT overnight. After the removal of DMF in vacuo, the residue is dissolved in EtOAc (100 mL) and washed with water (1×10 mL) and brine (2×10 mL). The organic layer is dried over anhydrous Na2SO4 and concentrated in vacuo. The residue is purified by flash column chromatography (300 g silica gel, gradient elution: 10%-80% EtOAc in heptane) to give the pure product (22) as white solid (353 mg, 13%).

Workup

  1. customAfter the removal of DMF in vacuo
  2. dissolutionthe residue is dissolved in EtOAc (100 mL)
  3. washwashed with water (1×10 mL) and brine (2×10 mL)
  4. dry with materialThe organic layer is dried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by flash column chromatography (300 g silica gel, gradient elution: 10%-80% EtOAc in heptane)

Sources & evidence

ORD record
ord-aee245d67baf48b0b72300e5b75be1ff
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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