4-(2-Methylpiperidin-1-YL)-3-(trifluoromethyl)benzoic acid → HCID 178425424, compound

HRID 400771Notes

Reaction equation

HRID 400771 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]([OH:14])=O)=[CH:10][C:9]=1[C:17]([F:20])([F:19])[F:18].O[N:22]=[C:23]([C:25]1[CH:33]=[CH:32][C:28]2[NH:29][CH:30]=[N:31][C:27]=2[CH:26]=1)[NH2:24]>>[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]2[O:14][N:22]=[C:23]([C:25]3[CH:33]=[CH:32][C:28]4[NH:29][CH:30]=[N:31][C:27]=4[CH:26]=3)[N:24]=2)=[CH:10][C:9]=1[C:17]([F:19])([F:18])[F:20]

Participants

3

Reactant 2

HCID 594956554-(2-Methylpiperidin-1-YL)-3-(trifluoromethyl)benzoic acidHCID 178513241N'-hydroxy-3H-benzimidazole-5-carboximidamide

Product 1

HCID 178425424HCID 178425424, compound

Procedure

Title compound was prepared following general procedure 1 starting from Intermediate 11 (143 mg; 0.50 mmol) Intermediate 1 (88 mg; 0.50 mmol). Reaction mixture was filtered over a SPE-NH2 column, washed with THF followed by evaporation of the solvent under reduced pressure. Evaporation of the solvent gave a yellow oil which was recrystallized in a DCM/n-pentane mixture to give the title compound as an off-white solid. 1H NMR (DMSO, d6) δ 12.77 (s, 1H), 8.46 (dd, J=8.4, 2.1 Hz, 1H), 8.40 (m, 2H), 8.34 (s, 1H), 7.97 (dd, J=8.5, 1.6 Hz, 1H), 7.87 (d, J=8.5 Hz, 1H), 7.78 (d, J=8.5 Hz, 1H), 3.20-3.14 (m, 1H), 2.99-2.94 (m, 1H), 2.67-2.57 (m, 1H), 1.79 (m, 2H), 1.68-1.27 (m, 4H), 0.76 (d, 6 Hz, 3H). HPLC (Method A) Rt 4.51 min (Purity: 99.4%). LC/MS (method B): 428.3 (M+H)+.

Workup

  1. customTitle compound was prepared
  2. customReaction mixture
  3. filtrationwas filtered over a SPE-NH2 column
  4. washwashed with THF
  5. customfollowed by evaporation of the solvent under reduced pressure
  6. customEvaporation of the solvent
  7. customgave a yellow oil which
  8. customwas recrystallized in a DCM/n-pentane mixture

Sources & evidence

ORD record
ord-63c64e87049e4258bc2b25deb3c20f28
Source dataset
uspto-grants-2014_06
Patent number
US08741923B2

Reaction notes

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