Potassium Carbonate → HCID 178523832, compound

HRID 707326Notes

Reaction equation

HRID 707326 reaction equation
CC1C=CC(S(O[C@H:12]2[CH2:15][C@@H:14]([NH:16][C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])[CH2:13]2)(=O)=O)=CC=1.[O:27]1[C:35]2[C:30](=[N:31][CH:32]=[CH:33][CH:34]=2)[NH:29][C:28]1=[O:36].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.ClCCl>[O:36]=[C:28]1[N:29]([C@H:12]2[CH2:13][C@H:14]([NH:16][C:17](=[O:18])[O:19][CH2:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:15]2)[C:30]2=[N:31][CH:32]=[CH:33][CH:34]=[C:35]2[O:27]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2799900Oxazolo(4,5-b)pyridin-2(3H)-oneHCID 178427793HCID 178427793, compound

Product 1

HCID 178523832HCID 178523832, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of cis-3-(((benzyloxy)carbonyl)amino)cyclobutyl 4-methylbenzenesulfonate (0.25 g, 0.666 mmol) in dry dimethylformamide (1.332 ml) was added oxazolo[4,5-b]pyridin-2(3H)-one (0.091 g, 0.666 mmol) and potassium carbonate (0.230 g, 1.665 mmol). The resulting mixture was heated at 50° C. for 14 hours, 100° C. for 3 hours, then 110° C. for an additional 20 hours. The mixture was diluted with dichloromethane and washed with water and brine then dried with magnesium sulfate and evaporated to dryness under reduced pressure. The crude was advanced directly to next step.

Workup

  1. washwashed with water and brine
  2. dry with materialthen dried with magnesium sulfate
  3. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-78f708c72c734b7791758af71ca576c3
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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