Dimethylformamide → 2-Amino-6-chloroimidazo[1,2-b]pyridazine

HRID 1162426Notes

Reaction equation

N(C([C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[N:10][N:9]2[CH:15]=1)=O)=[N+]=[N-].C[N:17](C=O)C>O>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]2[N:9]([CH:15]=[C:6]([NH2:17])[N:7]=2)[N:10]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a 100-mL, round-bottomed flask was added azido(6-chloroimidazo[1,2-b]pyridazin-2-yl)methanone from Step 2 (2.3 g, 10 mmol) and DMF (40 mL). The solution was heated to 100° C. and H2O (1.8 mL, 100 mmol) was added. The mixture was stirred for 45 min and then allowed to cool to room temperature. The mixture was poured into water (150 mL) and then concentrated in vacuo. The solid residue was dissolved in 1:2 MeOH/CH2Cl2 (900 mL) and concentrated onto silica. Purification by silica gel chromatography (1 to 5% MeOH (2 M in NH3)/CH2Cl2) afforded the title compound as a yellow-green solid (0.71 g, 42% yield). MS (ESI positive ion) m/z: 169 (M+1). 1H NMR (400 MHz, DMSO-d6): δ ppm 7.69 (d, J=9.2 Hz, 1H), 7.37 (s, 1H), 7.05 (d, J=9.2 Hz, 1H), 5.74 (broad s, 2H).

Workup

temperatureto cool to room temperature
concentrationconcentrated in vacuo
dissolutionThe solid residue was dissolved in 1:2 MeOH/CH2Cl2 (900 mL)
concentrationconcentrated onto silica
customPurification by silica gel chromatography (1 to 5% MeOH (2 M in NH3)/CH2Cl2)

Sources & evidence

ORD record: ord-26ee004bc5eb4f29b3a1fe38c96eff54
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820665B2

Reaction notes

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