1-Bromo-2-methylpropane → HCID 178448507, compound

HRID 518626Notes

Reaction equation

HRID 518626 reaction equation
[N:1]1([CH2:7][CH2:8][O:9][C:10]2[N:15]=[CH:14][C:13]3[NH:16]/[C:17](=[N:25]\[C:26](=[O:33])[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)/[N:18]([CH:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)[C:12]=3[CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:41][CH:42]([CH3:44])[CH3:43]>CN(C=O)C>[CH2:41]([N:22]1[CH2:21][CH2:20][CH:19]([N:18]2[C:12]3[CH:11]=[C:10]([O:9][CH2:8][CH2:7][N:1]4[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]4)[N:15]=[CH:14][C:13]=3[NH:16]/[C:17]/2=[N:25]\[C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:24][CH2:23]1)[CH:42]([CH3:44])[CH3:43]

Participants

5

Reactant 3

HCID 65551-Bromo-2-methylpropaneHCID 11430Potassium CarbonateHCID 178522618HCID 178522618, compound

Product 1

HCID 178448507HCID 178448507, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of (E)-N-(6-(2-(piperidin-1-yl)ethoxy)-1-(piperidin-4-yl)-1H-imidazo[4,5-c]pyridin-2(3H)-ylidene)benzamide (0.089 g, 0.198 mmol) and potassium carbonate (0.082 g, 0.595 mmol) in DMF (2 mL) was cooled to 0° C. under nitrogen. To this mixture was added 1-bromo-2-methylpropane (0.054 g, 0.397 mmol). The ice bath was removed, and the resulting mixture was stirred for 16 hours at RT. The reaction mixture was diluted with water (10 mL) and DCM (30 mL), and the organic layer was collected, concentrated and purified by silica gel chromatography (5-30% MeOH/DCM) to afford (E)-N-(1-(1-isobutylpiperidin-4-yl)-6-(2-(piperidin-1-yl)ethoxy)-1H-imidazo[4,5-c]pyridin-2(3H)-ylidene)benzamide as an off-white solid (20 mg, 19.97% yield). MS m/z=505.2 [M+H]. Calc'd for C29H40N6O2: 504.3.

Workup

  1. customThe ice bath was removed
  2. additionThe reaction mixture was diluted with water (10 mL) and DCM (30 mL)
  3. customthe organic layer was collected
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (5-30% MeOH/DCM)

Sources & evidence

ORD record
ord-ab6f9991c7464f2a9f293e3260b1dbd7
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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