Water → HCID 69890377, compound

HRID 1168251Notes

Reaction equation

HRID 1168251 reaction equation
[NH2:1][C:2]1[N:7]2[CH:8]=[C:9]([CH2:11][CH3:12])[N:10]=[C:6]2[C:5]([C:13]([NH:15][CH2:16][CH:17]2[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH2:18]2)=[O:14])=[CH:4][CH:3]=1.[Cl:27]N1C(=O)CCC1=O.O>C(O)C>[NH2:1][C:2]1[N:7]2[C:8]([Cl:27])=[C:9]([CH2:11][CH3:12])[N:10]=[C:6]2[C:5]([C:13]([NH:15][CH2:16][CH:17]2[CH2:18][CH2:19][N:20]([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:21][CH2:22]2)=[O:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 22992227HCID 22992227, compound

Product 1

HCID 69890377HCID 69890377, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-amino-N-[(1-butylpiperidin-4-yl)methyl]-2-ethylimidazo[1,2-a]pyridine-8-carboxamide (EXAMPLE 10, Step 4, 170 mg, 0.48 mmol) in ethanol (4 mL) was added N-chlorosuccinimide (76 mg, 0.57 mmol) at room temperature. After stirring at room temperature for 1 h, water (50 mL) was added to the mixture. The aqueous layer was extracted with dichloromethane (60 mL×3). The combined organic layer was dried over magnesium sulfate and concentrated in vacuo. The residue was suspended in diethyl ether and the insoluble solid was collected by filtration to give 71 mg (38%) of the title compound as a gray solid.

Workup

  1. extractionThe aqueous layer was extracted with dichloromethane (60 mL×3)
  2. dry with materialThe combined organic layer was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. filtrationthe insoluble solid was collected by filtration

Sources & evidence

ORD record
ord-7a3b3a2560614351a041a3085299355d
Source dataset
uspto-grants-2003_09
Patent number
US06624162B2

Reaction notes

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