Nitrogen → HCID 25182019, compound

HRID 2037396Notes

Reaction equation

HRID 2037396 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2([CH3:15])[O:13][C:12](=[O:14])[NH:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.Br[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[N:18]=1.C([O-])([O-])=O.[K+].[K+].N#N>[Cu]I.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2([CH3:15])[O:13][C:12](=[O:14])[N:11]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N:23]4[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]4)[N:18]=3)[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 71645972-Bromo-6-(piperidin-1-yl)pyridineHCID 58109191HCID 58109191, compound

Product 1

HCID 25182019HCID 25182019, compoundYield 43.2%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
130 °C

Procedure

A mixture of 6-(3-chlorophenyl)-6-methyl-1,3-oxazinan-2-one (28 mg, 0.12 mmol), 2-bromo-6-piperidinopyridine (33 mg, 0.14 mmol), CuI (7 mg, 0.037 mmol), powdered K2CO3 (19 mg, 0.14 mmol) and CH2Cl2 (0.25 mL) was heated to 130 C under a stream of N2 such that the CH2Cl2 evaporated. The vessel was sealed and the mixture was heated at 130° C. for 1 h under N2. The residue was dissolved in MeCN (0.5 mL) and DMSO (0.5 mL) and purified by prep HPLC to afford 6-(3-chlorophenyl)-6-methyl-3-(6-(piperidin-1-yl)pyridin-2-yl)-1,3-oxazinan-2-one (20 mg) as a brown oil. LC-MS Method 1, tR=2.08 min, m/z=386, 388. 1H NMR (CDCl3) 1.62 (6H), 1.73 (s, 3H), 2.35 (m, 1H), 2.48 (m, 1H), 3.43 (5H), 4.11 (m, 1H), 6.50 (d, 1H), 7.20-7.60 (6H).

Workup

  1. customevaporated
  2. customThe vessel was sealed
  3. dissolutionThe residue was dissolved in MeCN (0.5 mL)
  4. customDMSO (0.5 mL) and purified by prep HPLC

Sources & evidence

ORD record
ord-7e993a6217b745eb91221e1d15dca89d
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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