Piperidine → 3-Piperidin-1-yl-propane-1-sulfonic acid [4-(8-methyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-amide

HRID 1824556Notes

Reaction equation

HRID 1824556 reaction equation
[CH3:1][C:2]1[C:3]2[N:4]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][S:18]([CH2:21][CH2:22][CH2:23]Cl)(=[O:20])=[O:19])=[CH:13][CH:12]=3)[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[NH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>>[CH3:1][C:2]1[C:3]2[N:4]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][S:18]([CH2:21][CH2:22][CH2:23][N:25]4[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]4)(=[O:20])=[O:19])=[CH:13][CH:12]=3)[N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 8082PiperidineHCID 865841763-Chloro-propane-1-sulfonic acid [4-(8-methyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-amide

Product 1

HCID 101364233-Piperidin-1-yl-propane-1-sulfonic acid [4-(8-methyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-amide

Procedure

The product of Step A (65 mg) and piperidine (1.0 mL) were heated at 100° C. for 1.5 hours. The reaction was cooled to ambient temperature and partitioned between ethyl acetate (15 mL) and saturated sodium bicarbonate solution (15 mL). The aqueous portion was extracted with a fresh portion of ethyl acetate (15 mL) (2×) and the organic portions combined and washed with brine (15 mL). The organic portions were dried over magnesium sulfate, filtered and evaporated. The residue was purified via silica gel chromatography (dichloromethane/methanol) to give the title compound (26 mg). ). 1H-NMR (CD3OD) δ 1H-NMR (CD3OD) δ8.14 (d, J=7.0 Hz, 1H), 8.00 (s, 1H), 7.81 (m, 2H), 7.23 (m, 2H), 6.98 (m, 1H), 6.70 (t, J=7.0 Hz, 1H), 3.07 (m, 2H), 2.49 (s, 3H), 2.31 (m, 6H), 1.87 (m, 2H), 1.44 (m, 4H), 1.33 (m, 2H).

Workup

  1. custompartitioned between ethyl acetate (15 mL) and saturated sodium bicarbonate solution (15 mL)
  2. extractionThe aqueous portion was extracted with a fresh portion of ethyl acetate (15 mL) (2×)
  3. washwashed with brine (15 mL)
  4. dry with materialThe organic portions were dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified via silica gel chromatography (dichloromethane/methanol)

Sources & evidence

ORD record
ord-bc51d39f06354f68a9efada105004296
Source dataset
uspto-grants-2006_05
Patent number
US07041828B2

Reaction notes

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