Potassium Carbonate → HCID 68912506, compound

HRID 1986854Notes

Reaction equation

HRID 1986854 reaction equation
I[CH2:2][C@@H:3]([CH3:16])[CH2:4][N:5]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][CH2:7][C:6]1=[O:15].[CH:17]1([CH2:20][O:21][CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH2:19][CH2:18]1.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH:17]1([CH2:20][O:21][CH:22]2[CH2:27][CH2:26][N:25]([CH2:2][C@@H:3]([CH3:16])[CH2:4][N:5]3[C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=4[O:8][CH2:7][C:6]3=[O:15])[CH2:24][CH2:23]2)[CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 171780104-(Cyclopropylmethoxy)piperidineHCID 68912224(S)-4-(3-Iodo-2-methylpropyl]-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 68912506HCID 68912506, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A reaction flask was charged with (S)-4-(3-Iodo-2-methylpropyl]-4H-benzo[1,4]oxazin-3-one (0.199 g, 0.6 mmol), 4-cyclopropylmethoxypiperidine (0.093 g, 0.6 mmol), and K2CO3 (0.124 g, 0.9 mmol) in MeCN (2 mL) and stirred at 50° for 3 days. The reaction mixture was quenched with water and the product extracted into EtOAc. The combined organic phases were dried over Na2SO4, filtered, and concentrated. The product was purified by cation exchange column chromatography followed by flash column chromatography (SiO2; EtOAc) to give the title compound (0.138 g, 64%). 1H NMR (CDCl3) d 6.99-6.97 (m, 1H), 6.85-6.79 (m, 3H), 4.47-4.35 (m, 2H), 3.85-3.74 (m, 2H), 3.14-3.08 (m, 1H), 3.11 (d, J=6.8 Hz, 2H), 2.64-2.61 (m, 1H), 2.49-2.46 (m, 1H), 2.10-2.04 (m, 2H), 2.00-1.68 (m, 6H), 1.47-1.38 (m, 2H), 0.90-0.84 (m, 1H), 0.71 (d, J=6.6 Hz, 3H), 0.37-0.33 (m, 2H), 0.04-0.00 (m, 2H); 13C NMR (CDCl3) d 164.6, 145.4, 128.5 123.4, 122.4, 116.9, 115.3, 75.0, 72.5, 67.5, 63.3, 52.6, 51.6, 45.0, 31.6, 31.5, 29.1, 16.7, 10.9, 2.9.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionthe product extracted into EtOAc
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was purified by cation exchange column chromatography

Sources & evidence

ORD record
ord-68d54570091646d68ccc280a57a0b8fa
Source dataset
uspto-grants-2009_06
Patent number
US07550459B2

Reaction notes

Loading…