2-Methylquinoline → (E)-tert-Butyl 4-(8-morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-b]pyridazin-3-yl)piperidine-1-carboxylate

HRID 718640Notes

Reaction equation

HRID 718640 reaction equation
[CH:1]([C:3]1[N:4]=[C:5]2[C:10]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[CH:9][CH:8]=[N:7][N:6]2[C:17]=1[CH:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]1)=O.[CH3:31][C:32]1[CH:41]=[CH:40][C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[N:33]=1.Br[Si](C)(C)C>CN(C=O)C>[O:14]1[CH2:13][CH2:12][N:11]([C:10]2[C:5]3[N:6]([C:17]([CH:18]4[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]4)=[C:3](/[CH:1]=[CH:31]/[C:32]4[CH:41]=[CH:40][C:39]5[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=5)[N:33]=4)[N:4]=3)[N:7]=[CH:8][CH:9]=2)[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 70602-MethylquinolineHCID 76113BromotrimethylsilaneHCID 117733831tert-Butyl 4-(2-formyl-8-morpholinoimidazo[1,2-b]pyridazin-3-yl)piperidine-1-carboxylate

Product 1

HCID 117732502(E)-tert-Butyl 4-(8-morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-b]pyridazin-3-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of compound 41c (0.40 g, 0.96 mmol), 2-methylquinoline (0.17 g, 1.2 mmol) and bromotrimethylsilane (0.32 g, 2.9 mmol) in DMF (4 mL) was stirred at 80° C. for 5 h and allowed to cool to rt. The solids formed were collected by filtration, and washed with methanol (50 mL) to obtain compound 48a as a brown solid. Mass Spectrum (LCMS, ESI pos.): Calcd. for C31H36N6O3: 541.3 (M+H). Found: 541.2.

Workup

  1. customThe solids formed
  2. filtrationwere collected by filtration
  3. washwashed with methanol (50 mL)

Sources & evidence

ORD record
ord-b8c567fd32d24518af20b71c8f138d21
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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