3,6-Dichloropyridazine → HCID 58299919, compound

HRID 875940Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][CH:7]=1.[C:9]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][C@H:17]1[CH3:22])([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].C(N(CC)C(C)C)(C)C>C(OCC)(=O)C>[Cl:1][C:2]1[N:3]=[N:4][C:5]([N:19]2[CH2:20][CH2:21][N:16]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@H:17]([CH3:22])[CH2:18]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 3,6-dichloropyridazine (298 mg, 2 mmol) and (R)-1-N-Boc-2-methyl piperazine (401 mg, 2.0 mmol) in N,N-diisopropylethylamine (0.7 mL, 4 mmol) was stirred at 120° C. for 5 h. The reaction mixture was diluted with ethyl acetate and washed with brine (2×), then dried over MgSO4. The salts were removed by filtration and the filtrate was concentrated and the residue was purified by chromatography on silica gel eluting with 20% to 80% ethyl acetate in hexane to give compound 11as a light yellow solid (511 mg, 82%). 1H NMR (500 MHz, CD3OD) δ 7.24 (1H, d, J=10 Hz), 6.88 (1H, d, J=10 Hz), 4.38 (1H, br s), 4.17 (1H, d, J=10 Hz), 4.05-3.97 (2H, m), 3.39 (1H, dd, J=15 Hz, J=5 Hz), 3.29 (1H, ddd, J=15 Hz, J=10 Hz, J=5 Hz), 1.51 (9H, s), 1.21 (3H, d, J=10 Hz) ppm; LCMS-ESI (POS), M/Z, M+1: Found 313.1, Calculated 313.1.

Workup

washwashed with brine (2×)
dry with materialdried over MgSO4
customThe salts were removed by filtration
concentrationthe filtrate was concentrated
customthe residue was purified by chromatography on silica gel eluting with 20% to 80% ethyl acetate in hexane

Sources & evidence

ORD record: ord-a5473017372c4733a1ad5c59b00842be
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08980903B2

Reaction notes

Loading…