Sodium Hydroxide → tert-Butyl 4-(2-formyl-8-morpholinoimidazo[1,2-b]pyridazin-3-yl)piperidine-1-carboxylate

HRID 718628Notes

Reaction equation

HRID 718628 reaction equation
[OH:1][CH2:2][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.I(C1C=CC=CC=1C(O)=O)(=O)=O.[OH-].[Na+]>CS(C)=O>[CH:2]([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[CH2:19][CH2:20][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:22][CH2:23]1)=[O:1]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 1087942-Iodoxybenzoic acidHCID 117733827tert-Butyl 4-(2-(hydroxymethyl)-8-morpholinoimidazo[1,2-b]pyridazin-3-yl)piperidine-1-carboxylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of compound 41b (3.2 g, 7.7 mmol) in DMSO (22 mL) was added 2-iodoxybenzoic acid (3.4 g, 12 mmol) in portions. The reaction mixture was stirred overnight at rt and treated with 1N NaOH (50 mL). The solids formed were collected by filtration and washed with Et2O (2×50 mL) to obtain compound 41c as an off-white solid. Mass Spectrum (LCMS, ESI pos.): Calcd. for C21H29N5O4: 416.2 (M+H). found: 416.2.

Workup

  1. customThe solids formed
  2. filtrationwere collected by filtration
  3. washwashed with Et2O (2×50 mL)

Sources & evidence

ORD record
ord-bb127386da164cb8bf0e053777e45938
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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