Morpholine → HCID 24956520, compound

HRID 417937Notes

Reaction equation

HRID 417937 reaction equation
[CH3:1][C:2]1([CH3:24])CN[C:6](=[O:9])[C:5]2[S:10][C:11]([N:13]3[C:18]4[CH:19]=[C:20](O)[CH:21]=[CH:22][C:17]=4[O:16][CH2:15][CH2:14]3)=[N:12][C:4]=2[CH2:3]1.[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.[CH3:31]C(C)([O-])C.[Na+]>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:24][C:2]1([CH3:31])[CH2:3][C:4]2[N:12]=[C:11]([N:13]3[C:18]4[CH:19]=[C:20]([N:25]5[CH2:30][CH2:29][O:28][CH2:27][CH2:26]5)[CH:21]=[CH:22][C:17]=4[O:16][CH2:15][CH2:14]3)[S:10][C:5]=2[C:6](=[O:9])[CH2:1]1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 23676156Sodium t-butoxideHCID 24956160HCID 24956160, compound

Product 1

HCID 24956520HCID 24956520, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
140 °C

Procedure

Using Example 7 (50 mg, 0.14 mmol), morpholine (1.2 mL, 1.15 mmol), sodium tert-butoxide (41 mg, 0.43 mmol), palladium(II) acetate (2 mg, 0.007 mmol) and (But)3PBF4 (0.004 g, 0.014 mmol) in THF (3 mL) heated to 140° C. under microwave irradiation, for 60 min. The crude material was purified by prep HPLC to give the title compound as an off-white solid (5 mg, 11%). δH (CDCl3) 1.15 (6H, s), 2.43 (2H, s), 2.75 (2H, s), 3.04-3.12 (4H, m), 3.83-3.91 (4H, m), 4.20-4.25 (2H, m), 4.26-4.31 (2H, m), 6.70 (1H, dd, J 9.0, 2.8 Hz), 6.89 (1H, d, J 9.0 Hz), 7.41 (1H, d, J 2.6 Hz). LCMS (ES+) 400 (M+H)+.

Workup

  1. customThe crude material was purified by prep HPLC

Sources & evidence

ORD record
ord-316482b99ba54d69825952139dcdf9ce
Source dataset
uspto-grants-2012_01
Patent number
US08093238B2

Reaction notes

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