Potassium Carbonate → HCID 68912847, compound

HRID 1986850Notes

Reaction equation

HRID 1986850 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:10]2[CH:11]=[CH:12][CH:13]=[C:14]([CH2:15][CH3:16])[C:9]=2[O:8][CH2:7][C:6]1=[O:17].[CH:18]1([CH2:21][O:22][CH:23]2[CH2:29][CH:28]3[NH:30][CH:25]([CH2:26][CH2:27]3)[CH2:24]2)[CH2:20][CH2:19]1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH:18]1([CH2:21][O:22][CH:23]2[CH2:24][CH:25]3[N:30]([CH2:2][CH2:3][CH2:4][N:5]4[C:10]5[CH:11]=[CH:12][CH:13]=[C:14]([CH2:15][CH3:16])[C:9]=5[O:8][CH2:7][C:6]4=[O:17])[CH:28]([CH2:27][CH2:26]3)[CH2:29]2)[CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 57927696HCID 57927696, compoundHCID 68908046HCID 68908046, compound

Product 1

HCID 68912847HCID 68912847, compoundYield 20.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A 7 ml vial was charged with 4-(3-chloropropyl)-8-ethyl-4H-benzo[1,4]oxazin-3-one (0.21 g, 0.83 mmol), 3-cyclopropylmethoxy-8-aza-bicyclo[3,2,1]octane (0.16 g, 0.87 mmol), K2CO3 (0.23 g, 1.7 mmol), acetonitrile (4 ml) a shaken at 60° C. for 90 hours The reaction mixture was evaporated to dryness and purified by prep TLC (SiO2; heptanes/EtOAc 1:1) followed by Prep HPLC to give the title compound (0.068 g, 20.5%). 1H NMR (CDCl3) 1H NMR (CDCl3) d 7.05-6.84 (m, 3H), 4.56 (s, 2H), 4.04-3.98 (m, 2H), 3.53-3.49 (m, 1H), 3.19-3.11 (m, 4H), 2.67-2.59 (m,2H), 2.42-2.37 (m, 2H), 2.07-1.74 (m, 1OH), 1.21-1.15 (m, 3H), 1.06-0.93 (m, 1H), 0.51-0.44 (m, 2H), 0.21-0.14 (m, 2H); 13C NMR (CDCl3) d 164.60, 143.25, 133.02, 128.66, 123.99, 122.32, 113.20, 72.78, 72.23, 67.74, 58.59, 49.56, 39.83, 35.73, 26.45, 26.17, 23.03, 14.50, 11.04, 2.94.

Workup

  1. customwas evaporated to dryness
  2. custompurified by prep TLC (SiO2; heptanes/EtOAc 1:1)

Sources & evidence

ORD record
ord-e967f869980b4ccda85cb9893f02941b
Source dataset
uspto-grants-2009_06
Patent number
US07550459B2

Reaction notes

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