Acetonitrile → HCID 49839765, compound

HRID 1396024Notes

Reaction equation

HRID 1396024 reaction equation
C(O)=O.[Cl:4][C:5]1[CH:24]=[CH:23][C:8]([O:9][C:10]2[CH:11]=[C:12]([CH:20]=[CH:21][CH:22]=2)[O:13][CH2:14][CH2:15][CH:16]2[CH2:19][NH:18][CH2:17]2)=[CH:7][CH:6]=1.CC#N.C1([O:34][C:35](=O)[NH:36][C:37]2[N:41]3[N:42]=[CH:43][CH:44]=[CH:45][C:40]3=[N:39][CH:38]=2)C=CC=CC=1>CCOC(C)=O>[N:39]1[CH:38]=[C:37]([NH:36][C:35]([N:18]2[CH2:17][CH:16]([CH2:15][CH2:14][O:13][C:12]3[CH:20]=[CH:21][CH:22]=[C:10]([O:9][C:8]4[CH:7]=[CH:6][C:5]([Cl:4])=[CH:24][CH:23]=4)[CH:11]=3)[CH2:19]2)=[O:34])[N:41]2[C:40]=1[CH:45]=[CH:44][CH:43]=[N:42]2

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 58442681Imidazo[1,2-b]pyridazin-3-yl-carbamic acid phenyl esterHCID 66974078HCID 66974078, compound

Product 1

HCID 49839765HCID 49839765, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution consisting of 3-{2-[3-(4-chloro-phenoxy)-phenoxy]-ethyl}-azetidine formic acid salt (0.040 g, 0.13 mmol), TEA (0.018 mL, 0.13 mmol) and CH3CN (1.0 mL) was added imidazo[1,2-b]pyridazin-3-yl-carbamic acid phenyl ester (0.034 g, 0.13 mmol). The reaction mixture was stirred at room temperature for 16 h, then diluted with EtOAc (40 mL) and washed with saturated aq. NaHCO3 (40 mL). The organic layer was dried (Na2SO4) and concentrated. The crude residue was purified (FCC) to give the title compound (0.035 g, 57%). MS (ESI+): calcd. for C24H22ClN5O3, 463.14. m/z found, 464.1 (M+H)+. 1H NMR (d6-DMSO): 8.55 (s, 1H), 8.52 (d, J=4.4 Hz, 1H), 8.06 (d, J=9.2 Hz, 1H), 7.64 (s, 1H), 7.43 (d, J=7.3 Hz, 2H), 7.29 (t, J=8.2 Hz, 1H), 7.19-7.15 (m, 1H), 7.04 (d, J=7.4 Hz, 2H), 6.75 (d, J=8.3 Hz, 1H), 6.61-6.55 (m, 2H), 4.09 (t, J=8.1 Hz, 2H), 3.99 (t, J=6.1 Hz, 2H), 3.77-3.66 (m, 2H), 2.83-2.69 (m, 1H), 2.10-2.01 (m, 2H).

Workup

  1. washwashed with saturated aq. NaHCO3 (40 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude residue was purified (FCC)

Sources & evidence

ORD record
ord-985a010ef28742829afa7fcdd681ecd7
Source dataset
uspto-grants-2014_12
Patent number
US08901111B2

Reaction notes

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