HCID 67028741, compound → HCID 67029115, compound

HRID 455150Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][N:11]3[C:16]=2[CH2:17][N:18]2[CH2:22][C:21](OC)=[CH:20][C:19]2=[O:25])=[CH:4][CH:3]=1>CN(C)CCN.Cl.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][N:11]3[C:16]=2[CH2:17][N:18]2[CH2:22][C:21]([NH:9][CH2:8][CH2:16][N:11]([CH3:12])[CH3:10])=[CH:20][C:19]2=[O:25])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 140 °C

Procedure

To a mixture of 100 mg of 1-((2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)methyl)-4-methoxy-1H-pyrrol-2(5H)-one (0.251 mmol, 1 eq) in 1 mL of N,N-dimethylethane-1,2-diamine in a sealed tube, one drop of HCl was added. The solution was heated at 140° C., O/N. The mixture was then diluted with EtOAc, washed with an excess of NaHCO3 (aq, sat), dried on MgSO4, filtered and concentrated. The crude was purified on silica gel chromatography (MeOH:NH4OH (95:5)/EtOAc, 0 to 15%). The product was then washed with ether to give a white solid. (37 mg, 32%) m/e+=410 (M+H+). 1H-NMR (400 MHz, CDCl3, δ): 8.51 (d, 1H, D, J=6.6 Hz), 7.72 (d, 2H, D, J=8.6 Hz), 7.61 (d, 1H, D, J=9.2 Hz), 7.45 (d, 2H, D, J=8.4 Hz), 7.24 (t, 1H, D, J=8.8 Hz), 6.85 (t, 1H, D, J=6.4 Hz), 5.06 (s, 2H), 4.89 (m, 1H), 4.67 (s, 1H), 3.56 (s, 2H), 2.99 (m, 2H), 2.42 (m, 2H), 2.15 (s, 6H).

Workup

washwashed with an excess of NaHCO3 (aq, sat)
customdried on MgSO4
filtrationfiltered
concentrationconcentrated
customThe crude was purified on silica gel chromatography (MeOH:NH4OH (95:5)/EtOAc, 0 to 15%)
washThe product was then washed with ether
customto give a white solid

Sources & evidence

ORD record: ord-b57e7d4f1d4747a397c1c10a15b7c54e
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497278B2

Reaction notes

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