Potassium Carbonate → HCID 16753678, compound

HRID 1992434Notes

Reaction equation

[NH2:1][C:2]1[C:3]2[N:4]([C:8](=[S:28])[NH:9][C:10]=2[C:11]2[C:20]([F:21])=[C:19]3[C:14]([CH:15]=[CH:16][C:17]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[N:18]3)=[CH:13][CH:12]=2)[CH:5]=[CH:6][N:7]=1.Cl[C:30]1[N:35]=[CH:34][CH:33]=[CH:32][N:31]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:21][C:20]1[C:11]([C:10]2[N:9]=[C:8]([S:28][C:30]3[N:35]=[CH:34][CH:33]=[CH:32][N:31]=3)[N:4]3[CH:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]=23)=[CH:12][CH:13]=[C:14]2[C:19]=1[N:18]=[C:17]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH:16]=[CH:15]2

Participants

Conditions

Temperature: 100 °C

Procedure

A 10 mL microwave vessel was charged with a solution of 8-amino-1-(8-fluoro-2-phenyl-quinolin-7-yl)-2H-imidazo[1,5-a]pyrazine-3-thione (10 mg, 0.00002 mol), 2-chloropyrimidine (0.0059 g, 0.000052 mol) and potassium carbonate (0.011 g, 0.000077 mol) in DMF. The reaction mixture was heated in the microwave at 100° C. for 10 min followed by 120° C. for 10 min to get full consumption of SM. The reaction mixture was concentrated in vacuo. Purification by Gilson HPLC eluting with 10→60% acetonitrile: H2O afforded the title compound as a light yellow solid. 1H NMR (400 MHz, CDCl3): δ=7.07 (t, J=4.93 Hz, 1H), 7.21 (d, J=5.05 Hz, 1H), 7.48-7.59 (m, 4H), 7.74-7.85 (m, 2H), 8.04 (d, J=8.59 Hz, 1H), 8.25 (dd, J=8.21, 1.39 Hz, 2H), 8.31 (dd, J=8.72, 1.39 Hz, 1H), 8.50 (d, J=4.80 Hz, 2H). MS(ES+): m/z 465.98 (100)[MH+]. HPLC: tR=2.75 min (Open Lynx polar—5 min).

Workup

customto get full
customconsumption of SM
concentrationThe reaction mixture was concentrated in vacuo
customPurification by Gilson HPLC
washeluting with 10→60% acetonitrile

Sources & evidence

ORD record: ord-4d1ad5b9c283490fb9e10ea76ad71019
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07648987B2

Reaction notes

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