Aniline → HCID 24956519, compound

HRID 417936Notes

Reaction equation

HRID 417936 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.[NH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[CH3:32]C(C)([O-])C.[Na+]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:32][C:2]1([CH3:1])[CH2:3][C:4]2[N:12]=[C:11]([N:13]3[C:18]4[CH:19]=[C:20]([NH:25][C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[CH:21]=[CH:22][C:17]=4[O:16][CH2:15][CH2:14]3)[S:10][C:5]=2[C:6](=[O:9])[CH2:24]1

Participants

6

Reactant 3

HCID 6115AnilineHCID 23676156Sodium t-butoxideHCID 24956160HCID 24956160, compound

Product 1

HCID 24956519HCID 24956519, compoundYield 15.7%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

Using Example 7 (40 mg, 0.11 mmol), aniline (0.040 mL, 0.460 mmol), sodium tert-butoxide (28 mg, 028 mmol), palladium(II) acetate (4 mg, 0.010 mmol) and (But)3PBF4 (8 mg, 0.022 mmol) in DMF (3 mL) heated to 140° C. under microwave irradiation, for 40 min. The crude material was purified by prep HPLC to give the title compound as an off-white solid (7 mg, 15%). δH (CDCl3) 1.14 (6H, s), 2.42 (2H, s), 2.75 (2H, s) 4.13-4.20 (2H, m), 4.29-4.35 (2H, m), 5.61 (1H, br s), 6.80-6.93 (3H, m), 7.00-7.05 (2H, m), 7.23-7.31 (2H, m), 7.77 (1H, d, J 2.3 Hz). LCMS (ES+) 406 (M+H)+.

Workup

  1. customThe crude material was purified by prep HPLC

Sources & evidence

ORD record
ord-a515305568ab4378b2de4210c7245c57
Source dataset
uspto-grants-2012_01
Patent number
US08093238B2

Reaction notes

Loading…