5-Methyl-6-(2-methylpiperidin-1-yl)nicotinic acid → HCID 178423042, compound

HRID 400773Notes

Reaction equation

HRID 400773 reaction equation
[CH3:1][C:2]1[C:3]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]2[CH3:17])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=O.O[N:19]=[C:20]([C:22]1[CH:30]=[CH:29][C:25]2[NH:26][CH:27]=[N:28][C:24]=2[CH:23]=1)[NH2:21]>>[CH3:1][C:2]1[CH:10]=[C:6]([C:7]2[O:9][N:19]=[C:20]([C:22]3[CH:30]=[CH:29][C:25]4[NH:26][CH:27]=[N:28][C:24]=4[CH:23]=3)[N:21]=2)[CH:5]=[N:4][C:3]=1[N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[CH3:17]

Participants

3

Reactant 2

HCID 584433645-Methyl-6-(2-methylpiperidin-1-yl)nicotinic acidHCID 178513241N'-hydroxy-3H-benzimidazole-5-carboximidamide

Product 1

HCID 178423042HCID 178423042, compound

Procedure

Title compound was prepared following general procedure 1 starting from Intermediate 13 (120 mg; 0.51 mmol) and Intermediate 1 (90 mg; 0.51 mmol). Reaction mixture was filtered over a SPE-NH2 column, washed with THF followed by evaporation of the solvent under reduced pressure. Purification by silica column chromatography (EtOAc/c-Hex, 30/70 to 100/0) afforded the title compound as a brown powder. 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 2.71 min (Purity: 86.6%). 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. customPurification by silica column chromatography (EtOAc/c-Hex, 30/70 to 100/0)

Sources & evidence

ORD record
ord-63f608bafa0345158501ae4fdf20caaf
Source dataset
uspto-grants-2014_06
Patent number
US08741923B2

Reaction notes

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