Potassium Carbonate → HCID 25016595, compound

HRID 1878754Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][N:4]1[C:9](=[O:10])[CH:8]=[CH:7][C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:5]1.[Cl:17][C:18]1[CH:23]=[C:22](F)[CH:21]=[CH:20][N:19]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:17][C:18]1[CH:23]=[C:22]([NH:1][CH2:2][CH2:3][N:4]2[C:9](=[O:10])[CH:8]=[CH:7][C:6]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:5]2)[CH:21]=[CH:20][N:19]=1

Participants

Conditions

Temperature: 75 °C

Procedure

A suspension of 2-(2-aminoethyl)-6-phenylpyridazin-3(2H)-one (425 mg, 1.97 mmol), 2-chloro-4-fluoropyridine (312 mg, 2.37 mmol), and K2CO3 (546 mg, 3.95 mmol) in DMF (5 mL) was stirred under nitrogen at 75° C. for 3 days. The reaction mixture was partitioned between CH2Cl2 (40 mL) and 5% NaHCO3 (20 mL), and the aqueous was extracted with 9:1 CHCl3/iPrOH (3×25 mL). The combined organics was dried over MgSO4 and concentrated to a solid from toluene. The solid was triturated with toluene (2×5 mL) and diethyl ether (10 mL) to give a white solid. MS (ESI pos. ion) m/z (MH+): 327. Calc'd exact mass for C17H15ClN4O: 326. 1H NMR (400 MHz, Chloroform-d) δ ppm 3.61-3.68 (m, 2 H) 4.52-4.59 (m, 2 H) 5.35 (br. s., 1 H) 6.37 (dd, J=5.77, 2.26 Hz, 1 H) 6.45 (d, J=2.01 Hz, 1 H) 7.05 (d, J=9.54 Hz, 1 H) 7.44-7.52 (m, 3 H) 7.66-7.78 (m, 3 H) 7.91 (d, J=6.02 Hz, 1 H).

Workup

customThe reaction mixture was partitioned between CH2Cl2 (40 mL) and 5% NaHCO3 (20 mL)
extractionthe aqueous was extracted with 9:1 CHCl3/iPrOH (3×25 mL)
dry with materialThe combined organics was dried over MgSO4
concentrationconcentrated to a solid from toluene
customThe solid was triturated with toluene (2×5 mL) and diethyl ether (10 mL)
customto give a white solid

Sources & evidence

ORD record: ord-19b1efbab2334610b0946679b49d0ef1
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314087B2

Reaction notes

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