Sodium Bicarbonate → N-(2-(1-(6-methylbenzo[d]oxazol-2-yl)piperidin-4-yloxy)phenyl)pyridine-2-sulfonamide

HRID 1750037Notes

Reaction equation

Cl[C:2]1[O:3][C:4]2[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.FC(F)(F)C(O)=O.[NH:19]1[CH2:24][CH2:23][CH:22]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[NH:32][S:33]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=2)(=[O:35])=[O:34])[CH2:21][CH2:20]1.C(=O)(O)[O-].[Na+]>CCO>[CH3:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([N:19]3[CH2:24][CH2:23][CH:22]([O:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[NH:32][S:33]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=4)(=[O:35])=[O:34])[CH2:21][CH2:20]3)[O:3][C:4]=2[CH:10]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Compound 21 is prepared using synthesis method 3: intermediate 2e (0.21 g, 1.25 mmol) and intermediate 6a are placed in 5 mL of EtOH in the presence of 0.3 g (3.58 mmol) of sodium bicarbonate, and the mixture is then stirred for 2 h at 80° C. After evaporation under reduced pressure the residue is taken up by water and extracted using AcOEt. After drying of the organic phases and reduction to dryness the residue obtained is triturated in a mixture of EtOH/Et2O and 0.32 g of solid is isolated by filtration (yield: 77%).

Workup

customsynthesis method 3
customAfter evaporation under reduced pressure the residue
extractionextracted
customAfter drying of the organic phases and reduction to dryness the residue
customobtained
customis triturated in a mixture of EtOH/Et2O

Sources & evidence

ORD record: ord-964d27838dff4c18993c7644b460451e
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156834B2

Reaction notes

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