Pyrrolidine → HCID 89656439, compound

HRID 930951Notes

Reaction equation

HRID 930951 reaction equation
[CH2:1]([S:3]([C:6]1[CH:7]=[CH:8][C:9](F)=[C:10]([C:12]2[C:13]3[CH:22]=[CH:21][NH:20][C:14]=3[C:15](=[O:19])[N:16]([CH3:18])[CH:17]=2)[CH:11]=1)(=[O:5])=[O:4])[CH3:2].[NH:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1>CS(C)=O>[CH2:1]([S:3]([C:6]1[CH:7]=[CH:8][C:9]([N:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)=[C:10]([C:12]2[C:13]3[CH:22]=[CH:21][NH:20][C:14]=3[C:15](=[O:19])[N:16]([CH3:18])[CH:17]=2)[CH:11]=1)(=[O:5])=[O:4])[CH3:2]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 89657574HCID 89657574, compound

Product 1

HCID 89656439HCID 89656439, compoundYield 35.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of Example 330a (90 mg, 0.27 mmol) and pyrrolidine (668 μL, 8.08 mmol) in 1 mL DMSO was heated at 160° C. under microwave conditions for 30 minutes. The product was purified by preparative HPLC (C18, 10-80% CH3CN/water (0.1% TFA)) to give the title compound (37 mg, 35.7% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm 12.07 (s, 1H), 7.61 (dd, J=8.8, 2.4 Hz, 1H), 7.48 (d, J=2.4 Hz, 1H), 7.26 (t, J=2.8 Hz, 1H), 7.20 (s, 1H), 6.95 (d, J=8.9 Hz, 1H), 5.99-5.94 (m, 1H), 3.56 (s, 3H), 3.16 (q, J=7.3 Hz, 2H), 3.06 (s, 4H), 1.69 (t, J=6.3 Hz, 4H), 1.10 (t, J=7.4 Hz, 3H). MS (ESI+) m/z 386.1 (M+H)+.

Workup

  1. customThe product was purified by preparative HPLC (C18, 10-80% CH3CN/water (0.1% TFA))

Sources & evidence

ORD record
ord-a48e87ba94d9427b9087de9a70f2e217
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

Loading…