HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Acetonitrile → Azetidine urea derivative 2

HRID 1396024
Notes
Print preview

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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 58442681Imidazo[1,2-b]pyridazin-3-yl-carbamic acid phenyl esterHCID 669740783-{2-[3-(4-Chloro-phenoxy)-phenoxy]-ethyl}-azetidine formic acid salt

Product 1

HCID 49839765Azetidine urea derivative 2Yield 58%

Reagents, catalysts & solvents 1

HCID 8857Ethyl Acetate
Solvent

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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08901111B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes