8-Chloro-3-methoxy-1,5-naphthyridine → HCID 59843031, compound

HRID 1878751Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][N:4]1[C:9](=[O:10])[CH:8]=[CH:7][C:6]([C:11]2[S:12][CH:13]=[C:14]([CH3:16])[CH:15]=2)=[N:5]1.Cl[C:18]1[CH:19]=[CH:20][N:21]=[C:22]2[C:27]=1[N:26]=[CH:25][C:24]([O:28][CH3:29])=[CH:23]2>CC(O)C>[CH3:29][O:28][C:24]1[CH:23]=[C:22]2[C:27]([C:18]([NH:1][CH2:2][CH2:3][N:4]3[C:9](=[O:10])[CH:8]=[CH:7][C:6]([C:11]4[S:12][CH:13]=[C:14]([CH3:16])[CH:15]=4)=[N:5]3)=[CH:19][CH:20]=[N:21]2)=[N:26][CH:25]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A suspension of 2-(2-aminoethyl)-6-(4-methylthiophen-2-yl)pyridazin-3(2H)-one (360 mg, 1530 μmol) and 8-chloro-3-methoxy-1,5-naphthyridine (298 mg, 1530 μmol) in iPrOH (5 mL) was heated to 100° C. in a sealed vial. After 3 h, the reaction mixture was partitioned between CH2Cl2 (30 mL) and 1M NaOH (10 mL). The organic layer was dried over MgSO4, concentrated to a solid, and purified on 40 gram of silica eluting with 0-60% of 6% (2M NH3 in MeOH)/CH2Cl2. The resulting oil was crystallized from ACN (0.5 mL). MS (ESI pos. ion) m/z (MH+): 394. Calc'd exact mass for C20H19N5O2S: 393. 1H NMR (400 MHz, Chloroform-d) δ ppm 2.28 (s, 3 H) 3.84 (q, J=6.06 Hz, 2 H) 3.93 (s, 3 H) 4.55 (t, J=6.06 Hz, 2 H) 6.56 (d, J=5.48 Hz, 1 H) 6.93-6.98 (m, 2 H) 7.02 (t, J=5.67 Hz, 1 H) 7.16 (d, J=1.17 Hz, 1 H) 7.46 (d, J=2.74 Hz, 1 H) 7.52 (d, J=9.78 Hz, 1 H) 8.40 (d, J=2.74 Hz, 1 H) 8.46 (d, J=5.28 Hz, 1 H).

Workup

customthe reaction mixture was partitioned between CH2Cl2 (30 mL) and 1M NaOH (10 mL)
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated to a solid
custompurified on 40 gram of silica eluting with 0-60% of 6% (2M NH3 in MeOH)/CH2Cl2
customThe resulting oil was crystallized from ACN (0.5 mL)

Sources & evidence

ORD record: ord-794b8a12c5074a1b961ab61069ee678b
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314087B2

Reaction notes

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