Potassium Carbonate → HCID 57721180, compound

HRID 1986407Notes

Reaction equation

HRID 1986407 reaction equation
Cl.Cl[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.[NH2:11][C:12]1[C:13]([C:17]2[N:18]([CH2:43][CH3:44])[C:19]3[CH:24]=[C:23]([O:25][C:26]4[CH:27]=[C:28]([NH:32][C:33]([C:35]5[CH:40]=[CH:39][C:38](=[O:41])[NH:37][CH:36]=5)=[O:34])[CH:29]=[CH:30][CH:31]=4)[N:22]=[CH:21][C:20]=3[N:42]=2)=[N:14][O:15][N:16]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[NH2:11][C:12]1[C:13]([C:17]2[N:18]([CH2:43][CH3:44])[C:19]3[CH:24]=[C:23]([O:25][C:26]4[CH:27]=[C:28]([NH:32][C:33]([C:35]5[CH:36]=[N:37][C:38]([O:41][CH2:3][CH2:4][N:5]6[CH2:10][CH2:9][O:8][CH2:7][CH2:6]6)=[CH:39][CH:40]=5)=[O:34])[CH:29]=[CH:30][CH:31]=4)[N:22]=[CH:21][C:20]=3[N:42]=2)=[N:14][O:15][N:16]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 68875466HCID 68875466, compound

Product 1

HCID 57721180HCID 57721180, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2-Chloroethylmorpholine hydrochloride (104 mg, 0.6 mmol) was added to a slurry of the product of Step 2 (135 mg, 0.3 mmol) and powdered K2CO3 (1 g) in DMF (2 mL) and the mixture was heated to 80° C. for 3 h. The mixture was cooled, diluted with H2O and extracted with EtOAc. The combined organic extracts were washed with H2O and brine, dried (MgSO4), filtered and the filtrate was concentrated to give a yellow oil which was purified by reverse phase HPLC to give the title compound (50 mg, 30%). 1H NMR (400 MHz, CD3OD) δ ppm 9.13 (s, 1H), 8.69 (s, 1H), 8.09 (d, J=9.3, 1H); 7.92 (s, 1H), 7.69 (d, J=8.0, 1H), 7.60-7.53 (m, 2H), 7.12 (d, J=8.0, 1H), 6.67 (d, J=9.4, 1H), 4.76 (br q, 2H), 4.53 (br m, 2H), 3.83-3.70 (m, 8H), 3.33 (m, 2H), 1.46 (br t, 3H). MS (ES+) m/e 572 [M+H]+.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with EtOAc
  3. washThe combined organic extracts were washed with H2O and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customto give a yellow oil which
  8. customwas purified by reverse phase HPLC

Sources & evidence

ORD record
ord-31ccd9d8523b4771ae7749092b647ff7
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

Loading…