Diisopropylethylamine → HCID 44816002, compound

HRID 2358998Notes

Reaction equation

HRID 2358998 reaction equation
[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH3:21])=[C:9]([NH:11][C:12]2[C:17]([O:18][CH3:19])=[CH:16][N:15]=[C:14](Cl)[N:13]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].Cl.Cl.[NH:24]1[CH2:29][CH2:28][CH:27]([CH2:30][C:31]2[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=2)[CH2:26][CH2:25]1.C(N(C(C)C)CC)(C)C>CC(O)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH3:21])=[C:9]([NH:11][C:12]2[C:17]([O:18][CH3:19])=[CH:16][N:15]=[C:14]([N:34]3[CH2:35][CH2:36][CH:31]([CH2:30][C:27]4[CH:26]=[CH:25][N:24]=[CH:29][CH:28]=4)[CH2:32][CH2:33]3)[N:13]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 179988404-[(Piperidin-4-yl)methyl]pyridine--hydrogen chloride (1/2)HCID 86657088HCID 86657088, compound

Product 1

HCID 44816002HCID 44816002, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of the product of Step 1 (166 mg, 0.543 mmol), 4-piperidin-4-ylmethylpyridine dihydrochloride (162 mg, 0.651 mmol) and diisopropylethylamine (1.5 mL) was irradiated in 2-propanol (1.5 mL), in a microwave oven, at 180° C. for 2.5 hrs. The mixture was cooled and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (Biotage system, MeOH/dichloromethane, 0%-15%) to give the product (165 mg, 68.2%) as a solid. 1H-NMR (600 MHz, CDCl3) δ=1.21 (2H, m), 1.28 (9H, s), 1.60 (2H, d, J=13.19), 1.74 (1H, m), 2.23 (3H, s), 2.49 (2H, d, J=7.35), 2.72 (2H, td, J=12.76, 1.51), 3.80 (3H, s), 4.64 (2H, d, J=13.35), 6.96 (1H, s), 6.99 (1H, dd, J=7.88, 1.9), 7.03 (2H, d, J=5.43), 7.08 (1H, d, J=8.15), 7.60 (1H, s), 8.27 (1H, d, J=1.9), 8.44 (2H, d, J=5.7), LC-ESMS observed [M+H]+ 446.2 (calcd 446.6).

Workup

  1. temperatureThe mixture was cooled
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel (Biotage system, MeOH/dichloromethane, 0%-15%)

Sources & evidence

ORD record
ord-19537573831a46238cbf862e15d85909
Source dataset
uspto-grants-2014_04
Patent number
US08685972B2

Reaction notes

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