Sodium Carbonate → HCID 178495953, compound

HRID 1623362Notes

Reaction equation

HRID 1623362 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][CH2:22][CH:23]4[CH2:28][C@H:27]([CH3:29])[O:26][C@H:25]([CH3:30])[CH2:24]4)[N:16]=3)[C:12]([Cl:31])=[CH:11][N:10]=2)[CH2:4][CH2:3]1.[CH3:32][O:33][CH2:34][CH2:35]OS(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>CS(C)=O>[Cl:31][C:12]1[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][CH2:22][CH:23]3[CH2:24][C@H:25]([CH3:30])[O:26][C@H:27]([CH3:29])[CH2:28]3)[N:16]=2)=[CH:14][C:9]([NH:8][C@H:5]2[CH2:6][CH2:7][C@H:2]([NH:1][CH2:35][CH2:34][O:33][CH3:32])[CH2:3][CH2:4]2)=[N:10][CH:11]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 86977Ethanol, 2-methoxy-, 1-(4-methylbenzenesulfonate)HCID 178461426HCID 178461426, compound

Product 1

HCID 178495953HCID 178495953, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
105 °C

Procedure

The mixture of N2′-(trans-4-aminocyclohexyl)-5′-chloro-N6-(((2R,6S)-2,6-dimethyl tetrahydro-2H-pyran-4-yl)methyl)-2,4′-bipyridine-2′,6-diamine Compound 284 (20 mg, 0.045 mmol), p-toluenesulfonic acid 2-methoxyethyl ester (14 mg, 0.06 mmol) and sodium carbonate (9.6 mg, 0.09 mmol) in 1 ml DMSO was heated in a reaction vessel at 105° C. in an oil bath for 3 h. Formation of desired product was confirmed by LCMS, MH+502/504, 0.58 min, with ˜50% conversion. Mixture was diluted with ethyl acetate, washed with water, dried over sodium sulfate, and concentrated. Crude product was purified by HPLC to give desired product as TFA salt. LCMS (m/z): 502.2/504.2, retention time=0.56 min.

Sources & evidence

ORD record
ord-fbb975dd94694a09afafc2d8741d762e
Source dataset
uspto-grants-2014_07
Patent number
US08778951B2

Reaction notes

Loading…