Sodium Iodide → 3-[(6-(Imidazol-1-yl)pyridazin-3-yl)oxy]-1-[(1,3-benzodioxol-5-yl)methyl]piperidine

HRID 1270461Notes

Reaction equation

[N:1]1([C:6]2[N:11]=[N:10][C:9]([O:12][CH:13]3[CH2:18][CH2:17][CH2:16][NH:15][CH2:14]3)=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.Cl[CH2:20][C:21]1[CH:29]=[CH:28][C:24]2[O:25][CH2:26][O:27][C:23]=2[CH:22]=1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CN(C=O)C>[N:1]1([C:6]2[N:11]=[N:10][C:9]([O:12][CH:13]3[CH2:18][CH2:17][CH2:16][N:15]([CH2:20][C:21]4[CH:29]=[CH:28][C:24]5[O:25][CH2:26][O:27][C:23]=5[CH:22]=4)[CH2:14]3)=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 3-[(6-(imidazol-1-yl)pyridazin-3-yl)oxy]piperidine (220 mg), 5-chloromethyl-1,3-benzodioxole (0.26 mL), K2CO3 (1.0 g), and NaI (0.1 g) in DMF (15 mL) was heated at 50° C. under N2 for 3 hours. After filtration and concentration in vacuo, the residual oil was dissolved in CH2Cl2 (100 mL), washed with water (20 mL×3) and brine, dried (MgSO4), and concentrated. Purification by column chromatography gave 3-[(6-(imidazol-1-yl)pyridazin-3-yl)oxy]-1-[(1,3-benzodioxol-5-yl)methyl]piperidine, (77 mg) as a white solid, NMR: (CDCl3) 8.30 (s, 1), 7.68 (s, 1), 7.52 (d, 1), 7.22 (s, 1), 7.16 (d, 1), 6.75 (s, 2), 5.90 (d, 2), 5.41 (m, 1), 3.46 (Abq, 2), 2.88 (d, 1), 2.58–2.48 (m, 2), 2.32 (m, 1), 2.10 (m, 1), 1.70–1.60 (m, 2) ppm.

Workup

filtrationAfter filtration and concentration in vacuo
dissolutionthe residual oil was dissolved in CH2Cl2 (100 mL)
washwashed with water (20 mL×3) and brine
dry with materialdried (MgSO4)
concentrationconcentrated
customPurification by column chromatography

Sources & evidence

ORD record: ord-9b1fb3ff8eb74fa9b342d02b2ce6fb3b
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07202263B2

Reaction notes

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