Piperidine → HCID 68755400, compound

HRID 1615253Notes

Reaction equation

HRID 1615253 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1/[CH:7]=[CH:8]/[C:9]1[C:17]2[C:12](=[CH:13][C:14]([CH:18]=O)=[CH:15][CH:16]=2)[N:11]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)[N:10]=1.[NH:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:28][C:27]1=[O:35].N1CCCCC1>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1/[CH:7]=[CH:8]/[C:9]1[C:17]2[C:12](=[CH:13][C:14](/[CH:18]=[C:28]3/[C:27](=[O:35])[NH:26][C:34]4[C:29]/3=[CH:30][CH:31]=[CH:32][CH:33]=4)=[CH:15][CH:16]=2)[N:11]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)[N:10]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 321710OxindoleHCID 86651951HCID 86651951, compound

Product 1

HCID 68755400HCID 68755400, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (E)-3-(2-(pyridin-2-yl)vinyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-6-carbaldehyde (25 mg, 0.0749 mmol), oxindole (10 mg, 0.0749 mmol), and MeOH (1 mL) was added piperidine (1 uL) and the reaction heated to 60° C. for 3 hours. The reaction was cooled to room temperature and the product yellow solid was precipitated with MeOH (1 mL) and then filtered to give 11 mg. The filtrate was purified by column chromatography (silica gel, 99:1 to 98:2 CH2Cl2/MeOH) to give an additional 6 mg of product (17 mg total, 50%). 1H NMR (400 MHz, CDCl3) δ 8.69-8.62 (m, 1H), 8.14 (d, J=8.3 Hz, 1H), 8.00-7.91 (m, 3H), 7.77 (d, J=8.1 Hz, 1H), 7.72 (t, J=8.3 Hz, 1H), 7.63 (d, J=16.9 Hz, 1H), 7.53 (m, 2H), 7.44 (b.s., 1H), 7.25-7.17 (m, 2H), 6.92-6.86 (m, 2H), 5.77 (d, J=10.6 Hz, 1H), 4.09 (d, J=9.6 Hz, 1H), 3.84-3.74 (m, 1H), 2.67-2.53 (m, 1H), 2.24-2.13 (m, 2H), 1.85-1.66 (m, 3H); MS ESI 449.2 [M+H]+, calcd for [C28H24N4O2+H]+ 449.20.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customthe product yellow solid was precipitated with MeOH (1 mL)
  3. filtrationfiltered
  4. customto give 11 mg
  5. customThe filtrate was purified by column chromatography (silica gel, 99:1 to 98:2 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-9c0f6cf35ca741e88f87d5a42c48e88c
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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