Diisopropylethylamine → HCID 69455591, compound

HRID 1293428Notes

Reaction equation

HRID 1293428 reaction equation
[CH2:1]([O:8][C:9](=[O:18])[NH:10][C:11]1([CH3:17])[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:20]1[CH:25]=[C:24]([C:26]#[N:27])[CH:23]=[CH:22][N:21]=1.C(N(C(C)C)CC)(C)C>O1CCOCC1>[CH2:1]([O:8][C:9](=[O:18])[NH:10][C:11]1([CH3:17])[CH2:16][CH2:15][N:14]([C:20]2[CH:25]=[C:24]([C:26]#[N:27])[CH:23]=[CH:22][N:21]=2)[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5686382-Chloro-4-cyanopyridineHCID 23282901Benzyl (4-methylpiperidin-4-yl)carbamate

Product 1

HCID 69455591HCID 69455591, compoundYield 55.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of (4-methyl-piperidin-4-yl)-carbamic acid benzyl ester (310 mg, 1.25 mmol, Example 30B), 2-chloro-4-cyanopyridine (250 mg, 1.8 mmol) and diisopropylethylamine (280 μL) in dioxane (6 mL) was heated in a sealed tube at 90° C. for 3 days. The reaction mixture was cooled, concentrated, and then flash chromatographed using a gradient of 5% ethyl acetate/hexane to 30% ethyl acetate/hexane to provide the titled compound (245 mg) as a colorless foam. MS (CI) m/z 350 (M+H)+; 1H NMR (300 MHz, MeOH-d4) δ 8.22 (d, 1H), 7.34 (m, 1H), 7.29 (m, 5H), 7.00 (s, 1H), 6.77 (d, 1H), 5.04 (s, 2H), 3.95-3.89 (m, 2H), 3.26 (m, 2H), 2.19-2.10 (m, 2H), 1.61-1.50 (m, 2H), 1.27 (s, 3H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. customflash chromatographed

Sources & evidence

ORD record
ord-f733d6d488ea4c10bfc17be37d25c8f5
Source dataset
uspto-grants-2007_07
Patent number
US07238724B2

Reaction notes

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