4-(2-Methylpiperidin-1-YL)-3-(trifluoromethyl)benzoic acid → HCID 67542189, compound

HRID 219913Notes

Reaction equation

HRID 219913 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:16]=[CH:15][C:11]([C:12](O)=O)=[CH:10][C:9]=1[C:17]([F:20])([F:19])[F:18].[NH2:21][C:22](=[N:34][OH:35])[C:23]1[CH:24]=[CH:25][C:26]([F:33])=[C:27]([CH:32]=1)[C:28]([O:30][CH3:31])=[O:29]>>[F:33][C:26]1[CH:25]=[CH:24][C:23]([C:22]2[N:21]=[C:12]([C:11]3[CH:15]=[CH:16][C:8]([N:3]4[CH2:4][CH2:5][CH2:6][CH2:7][CH:2]4[CH3:1])=[C:9]([C:17]([F:20])([F:19])[F:18])[CH:10]=3)[O:35][N:34]=2)=[CH:32][C:27]=1[C:28]([O:30][CH3:31])=[O:29]

Participants

3

Reactant 2

HCID 594956554-(2-Methylpiperidin-1-YL)-3-(trifluoromethyl)benzoic acidHCID 72307478Methyl 5-[amino(hydroxyimino)methyl]-2-fluorobenzoate

Product 1

HCID 67542189HCID 67542189, compound

Procedure

The title compound was prepared following procedure described for example 4, step 1, but starting from Intermediate 15 (106.09 mg; 0.50 mmol) and Intermediate 45 (106.09 mg; 0.50 mmol). The reaction mixture was filtered through a SPE NH2 column (2 g) and rinsed with ACN. The filtrate was passed through a SPE SCX column (2 g) and rinsed with ACN. After evaporation of the solvents, the crude product was purified by flash chromatography (c-hex/EtOAc: 9.5/0.5), affording the title compound. 1H NMR (DMSO-d6, 300 MHz) δ 8.58 (dd, J=7.0, 2.3 Hz, 1H), 8.46 (dd, J=8.3, 2.1 Hz, 1H), 8.41-8.36 (m, 2H), 7.87 (d, J=8.4 Hz, 1H), 7.62 (dd, 1H), 3.93 (s, 3H), 3.23-3.14 (m, 1H), 2.99-2.92 (m, 1H), 2.66-2.58 (m, 1H), 1.82-1.75 (m, 2H), 1.67-1.30 (m, 4H), 0.79 (d, J=6.1 Hz, 3H). LC/MS (Method B): 464.3 (M+H)+. HPLC (Method A) Rt 3.82 min (Purity: 99.9%).

Workup

  1. customThe title compound was prepared following procedure
  2. filtrationThe reaction mixture was filtered through a SPE NH2 column (2 g)
  3. washrinsed with ACN
  4. washrinsed with ACN
  5. customAfter evaporation of the solvents
  6. customthe crude product was purified by flash chromatography (c-hex/EtOAc: 9.5/0.5)

Sources & evidence

ORD record
ord-2753ffa2dacc44d38bd9460ebab7ebb6
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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