Potassium Carbonate → HCID 25016592, compound

HRID 1878752Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6](F)[CH:5]=[CH:4][N:3]=1.[NH2:9][CH2:10][CH2:11][N:12]1[C:17](=[O:18])[CH:16]=[CH:15][C:14]([C:19]2[S:20][CH:21]=[C:22]([CH3:24])[CH:23]=2)=[N:13]1.C([O-])([O-])=O.[K+].[K+].C([O-])(O)=O.[Na+]>CN(C=O)C.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([NH:9][CH2:10][CH2:11][N:12]2[C:17](=[O:18])[CH:16]=[CH:15][C:14]([C:19]3[S:20][CH:21]=[C:22]([CH3:24])[CH:23]=3)=[N:13]2)[CH:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 75 °C

Procedure

A suspension of 2-chloro-4-fluoropyridine (904 mg, 6.87 mmol), 2-(2-aminoethyl)-6-(4-methylthiophen-2-yl)pyridazin-3(2H)-one (1470 mg, 6.25 mmol), and K2CO3 (1727 mg, 12.5 mmol) in DMF (8 mL) was stirred at 75° C. for 4 h. The mixture was partioned between CH2Cl2 (100 mL) and 5% NaHCO3 (50 mL). The organic layer was dried over MgSO4, concentrated, then purified on 40 g silica eluting with 20>60% of 2M NH3 in MeOH/CH2Cl2. Product isolated as a white solid. MS (ESI pos. ion) m/z (MH+): 347. Calc'd exact mass for C16H15ClN4OS: 346. 1H NMR (400 MHz, Chloroform-d) δ ppm 2.29 (s, 3 H) 3.61 (q, J=5.35 Hz, 2 H) 4.44-4.51 (m, 2 H) 5.31 (br. s., 1 H) 6.46 (s, 1 H) 6.94-7.01 (m, 2 H) 7.19 (s, 1 H) 7.57 (d, J=9.54 Hz, 1 H) 7.91 (d, J=6.02 Hz, 1 H). 13C NMR (101 MHz, Chloroform-d) δ ppm 15.76, 42.71, 50.46, 106.06, 107.27, 123.73, 128.21, 129.82, 130.08, 138.12, 138.76, 141.69, 149.32, 152.31, 155.06, 160.44.

Workup

dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated
custompurified on 40 g silica eluting with 20>60% of 2M NH3 in MeOH/CH2Cl2
customProduct isolated as a white solid

Sources & evidence

ORD record: ord-0867912b31fe4aafb098f1b6df2c9130
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314087B2

Reaction notes

Loading…