Dimethylformamide → HCID 21084060, compound

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[CH:12]=[CH:11][C:10]3[C:15]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[S:17][C:9]2=3)=[CH:4][CH:3]=1.[C:29](=[O:32])([O-])[O-].[Cs+].[Cs+].Cl.ClCC[CH:39]1O[CH2:43][CH2:42][NH:41][CH2:40]1.[CH3:45]N(C=O)C>>[O:32]1[CH2:29][CH2:45][N:41]([CH2:40][CH2:39][O:1][C:2]2[CH:3]=[CH:4][C:5]([N:8]3[C:13](=[O:14])[CH:12]=[CH:11][C:10]4[C:15]([C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=5)=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[S:17][C:9]3=4)=[CH:6][CH:7]=2)[CH2:42][CH2:43]1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 10796Cesium carbonate

HCID 21084070HCID 21084070, compound

HCID 21914305HCID 21914305, compound

Product 1

HCID 21084060HCID 21084060, compound

Procedure

To a mixture of the compound of Example 89 (100 mg, 0.256 mmol) and caesium carbonate (202 mg, 0.62 mmol) in dry DMF (5 mL) was added 2-(chloroethyl)morpholine hydrochloride (58 mg, 0.31 mmol) and the reaction heated at 60° under nitrogen for 48 h. The reaction was partitioned between water and EtOAc, the EtOAc extracts dried (MgSO4) and concentrated in vacuo. The crude product was then purified by column chromatography on silica eluting with 0–5% MeOH in DCM to give the title compound as a white solid (68 mg). δH (CDCl3) 7.44–7.20 (8H, m), 7.04 (2H, d, J 9 Hz), 6.51 (1H, d, J 10 Hz), 4.15–4.03 (4H, m), 3.68 (4H, m), 2.79 (2H, t, J 6 Hz), 2.54 (4H, m), 1.05 (3H, t, J 7 Hz). LCMS (ES+) RT 2.53 minutes, 505 (M+H)+.