4-(2-Methylpiperidin-1-YL)-3-(trifluoromethyl)benzoic acid → HCID 67541716, compound

HRID 219911Notes

Reaction equation

HRID 219911 reaction equation
[NH2:1][C:2](=[N:14][OH:15])[C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[F:13].[CH3:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][N:18]1[C:23]1[CH:31]=[CH:30][C:26]([C:27](O)=O)=[CH:25][C:24]=1[C:32]([F:35])([F:34])[F:33]>>[F:13][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:3]=1[C:2]1[N:1]=[C:27]([C:26]2[CH:30]=[CH:31][C:23]([N:18]3[CH2:19][CH2:20][CH2:21][CH2:22][CH:17]3[CH3:16])=[C:24]([C:32]([F:35])([F:34])[F:33])[CH:25]=2)[O:15][N:14]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

3

Reactant 2

HCID 594956554-(2-Methylpiperidin-1-YL)-3-(trifluoromethyl)benzoic acidHCID 72307476Methyl 4-[amino(hydroxyimino)methyl]-3-fluorobenzoate

Product 1

HCID 67541716HCID 67541716, compound

Procedure

The title compound was prepared following procedure described for example 4, step 1, but starting from Intermediate 2 (106.09 mg; 0.50 mmol) and Intermediate 15 (143.64 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 suspended in ACN, filtrated and dried under vacuo, affording the title compound as a yellow solid. 1H NMR (DMSO-d6, 300 MHz) δ 8.45 (dd, J=8.5, 1.9 Hz, 1H), 8.38 (d, J=2.0 Hz, 1H), 8.34-8.29 (m, 1H), 8.01 (dd, J=8.1, 1.6 Hz, 1H), 7.94 (dd, J=10.9, 1.4 Hz, 1H), 7.87 (d, J=8.5 Hz, 1H), 3.92 (s, 3H), 3.20-3.13 (m, 1H), 2.98-2.94 (m, 1H), 2.66-2.58 (m, 1H), 1.81-1.76 (m, 2H), 1.63-1.27 (m, 4H), 0.79 (d, J=6.0 Hz, 3H). HPLC (Method A) Rt 6.60 min (Purity: 70.1%).

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. filtrationfiltrated
  7. customdried under vacuo

Sources & evidence

ORD record
ord-28a7bd832fe74bdbbb96a18808d231ed
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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