4-Fluorosalicylic acid → HCID 86696998, compound

HRID 1191314Notes

Reaction equation

HRID 1191314 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([OH:11])[CH:3]=1.[Cl-].[C:13]([C:15]1[N:19]([CH3:20])[N:18]=[C:17]([CH2:21][NH2+:22][CH3:23])[CH:16]=1)#[N:14].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>[C:13]([C:15]1[N:19]([CH3:20])[N:18]=[C:17]([CH2:21][N:22]([CH3:23])[C:6](=[O:8])[C:5]2[CH:9]=[CH:10][C:2]([F:1])=[CH:3][C:4]=2[OH:11])[CH:16]=1)#[N:14]

Participants

6

Reactant 4

HCID 676614-Fluorosalicylic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 866969991643141-20-1

Product 1

HCID 86696998HCID 86696998, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-fluoro-2-hydroxybenzoic acid 136 (500 mg, 3.2 mmol), (5-cyano-1-methyl-1H-pyrazol-3-yl)-N-methylmethanaminium chloride 137 (600 mg, 3.2 mmol), and HATU (1.4 g, 3.5 mmol) in DMF (21 mL) was added DIEA (2.8 mL, 16 mmol). After stirring at room temperature for 14 hours, the solution was concentrated and purified by column chromatography over silica gel eluting with heptane/ethyl acetate(0-75%) to afford compound 138 (370 mg, 40%) as a semi-solid. 1H NMR (400 MHz, 80° C., DMSO-d6) δ 10.08 (s, 1H) 7.19 (m, 1H) 6.94 (s, 1H) 6.70-6.59 (m, 2H) 4.52 (s, 2H) 3.98 (d, J=0.8 Hz, 3H) 2.86 (s, 3H). LCMS APCI m/z 298 [M+H]+.

Workup

  1. concentrationthe solution was concentrated
  2. custompurified by column chromatography over silica gel eluting with heptane/ethyl acetate(0-75%)

Sources & evidence

ORD record
ord-e58058d1c9d94caf918658ecffbaa678
Source dataset
uspto-grants-2014_03
Patent number
US08680111B2

Reaction notes

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