3-Cyano-4-(2-methylpiperidin-1-yl)benzoic acid → HCID 178425425, compound

HRID 400772Notes

Reaction equation

HRID 400772 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[CH3:18])[C:6]([OH:8])=O)#[N:2].O[N:20]=[C:21]([C:23]1[CH:31]=[CH:30][C:26]2[NH:27][CH:28]=[N:29][C:25]=2[CH:24]=1)[NH2:22]>>[NH:27]1[C:26]2[CH:30]=[CH:31][C:23]([C:21]3[N:20]=[C:6]([C:5]4[CH:9]=[CH:10][C:11]([N:12]5[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]5[CH3:18])=[C:3]([CH:4]=4)[C:1]#[N:2])[O:8][N:22]=3)=[CH:24][C:25]=2[N:29]=[CH:28]1

Participants

3

Reactant 2

HCID 594957013-Cyano-4-(2-methylpiperidin-1-yl)benzoic acidHCID 178513241N'-hydroxy-3H-benzimidazole-5-carboximidamide

Product 1

HCID 178425425HCID 178425425, compound

Procedure

Title compound was prepared following general procedure 1 starting from Intermediate 12 (122 mg; 0.50 mmol) and 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. Reaction mixture was extracted with ethyl acetate and combined organic phase was washed with brine, dried over magnesium sulfate and concentrated in vacuo to give a yellow oily residue. Purification by silica column chromatography (DCM/MeOH, 98/2 then 95/5) afforded the title compound as an off-white solid. 1H NMR (DMSO, d6): δ 12.78 (s, 1H), 8.39-8.37 (m, 2H), 8.31 (s, 1H), 8.24 (dd, J=8.8, 2.2 Hz, 1H), 7.95-7.92 (m, 1H), 7.78-7.75 (m, 1H), 7.32 (d, J=8.8 Hz, 1H), 4.23-4.22 (m, 1H), 3.38-3.35 (m, 2H), 1.82-1.57 (m, 6H), 1.17 (d, 6.6 Hz, 3H). HPLC (Method A) Rt 3.65 min (Purity: 95.1%). LC/MS (method B): 358.3 (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. customReaction mixture
  7. extractionwas extracted with ethyl acetate and combined organic phase
  8. washwas washed with brine
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated in vacuo
  11. customto give a yellow oily residue
  12. customPurification by silica column chromatography (DCM/MeOH, 98/2

Sources & evidence

ORD record
ord-9024d1c81e064387803ae8bb03d59529
Source dataset
uspto-grants-2014_06
Patent number
US08741923B2

Reaction notes

Loading…