Cesium carbonate → HCID 67107213, compound

HRID 1623698Notes

Reaction equation

CC1C=CC(S(O[CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[C:20]([C:32]([NH:34][C:35]3[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=3)=[O:33])[CH:19]=2)(=O)=O)=CC=1.[CH3:41][C:42]([O:45][C:46]([NH:48][C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])=[O:47])([CH3:44])[CH3:43].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C)C=O.O>[C:26]1([CH2:25][O:24][C:21]2[CH:22]=[CH:23][C:18]([O:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12][N:48]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[C:46]([O:45][C:42]([CH3:41])([CH3:43])[CH3:44])=[O:47])=[CH:19][C:20]=2[C:32]([NH:34][C:35]2[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=2)=[O:33])[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

Conditions

Temperature: 60 °C

Procedure

2-{[2-({4-[(Phenylmethyl)oxy]-3-[(3-pyridinylamino)carbonyl]phenyl}oxy)ethyl]oxy}ethyl 4-methylbenzenesulfonate (may be prepared as described in Description 76; 500 mg, 0.89 mmol) was dissolved in N,N-dimethylformamide (10 ml). Di-tert-butyl iminodicarbonate (193 mg, 0.89 mmol) and Cs2CO3 (290 mg, 0.89 mmol) were added. The reaction mixture was heated at 60° C. for 3 h. After cooling to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with water, brine, dried over Na2SO4, and concentrated under reduced pressure to yield the title compound as an oil. 360 mg.

Workup

temperatureAfter cooling to room temperature
extractionextracted with ethyl acetate
washThe combined organic extracts were washed with water, brine
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-7a82f2524f054fa6bad6e4488e2facc7
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778939B2

Reaction notes

Loading…