1,1'-Carbonyldiimidazole → 5-AMINO-6-CHLORO-N-[1-(3-METHOXYPROPYL)-4-PIPERIDINYL]IMIDAZO[1,2-a]PYRIDINE-8-CARBOXAMIDE

HRID 1168247Notes

Reaction equation

HRID 1168247 reaction equation
[NH2:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[C:5]([C:11]([OH:13])=O)=[CH:4][C:3]=1[Cl:14].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:27][O:28][CH2:29][CH2:30][CH2:31][N:32]1[CH2:37][CH2:36][CH:35]([NH2:38])[CH2:34][CH2:33]1>CN(C)C=O.ClCCl>[NH2:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[C:5]([C:11]([NH:38][CH:35]2[CH2:36][CH2:37][N:32]([CH2:31][CH2:30][CH2:29][O:28][CH3:27])[CH2:33][CH2:34]2)=[O:13])=[CH:4][C:3]=1[Cl:14]

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 120880915-Amino-6-chloroimidazo[1,2-a]pyridine-8-carboxylic acidHCID 120880931-(3-Methoxypropyl)-4-piperidinamine

Product 1

HCID 120880945-AMINO-6-CHLORO-N-[1-(3-METHOXYPROPYL)-4-PIPERIDINYL]IMIDAZO[1,2-a]PYRIDINE-8-CARBOXAMIDEYield 48%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of the 5-amino-6-chloroimidazo[1,2-a]pyridine-8-carboxylic acid (EXAMPLE 1, METHOD A, Step 4, 210 mg, 0.99 mmol) in N,N-dimethylformamide (5 mL) was added 1,1′-carbonyldiimidazole (177 mg, 1.09 mmol) and stirred at room temperature for 20 min. To this resulting solution was added 1-(3-methoxypropyl)-4-piperidinamine (A. Karasawa et al., WO 9950264, 188 mg, 1.09 mmol) and the mixture was stirred overnight under nitrogen at room temperature. The mixture was concentrated in vacuo, chromatographed on a column of silica gel eluting with dichloromethane/methanol/25% aqueous ammonia (95:5:0.5) to afford a yellow oil, which was dissolved in dichloromethane (300 mL), washed with water (75 mL×3), brine (75 mL) and dried over magnesium sulfate. After treatment with charcoal, removal of solvent gave a cream solid, which was recrystallized from diethyl ether to afford 175 mg (48%) of the title compound as a solid.

Workup

  1. stirringKarasawa et al., WO 9950264, 188 mg, 1.09 mmol) and the mixture was stirred overnight under nitrogen at room temperature
  2. concentrationThe mixture was concentrated in vacuo
  3. customchromatographed on a column of silica gel eluting with dichloromethane/methanol/25% aqueous ammonia (95:5:0.5)
  4. customto afford a yellow oil, which
  5. washwashed with water (75 mL×3), brine (75 mL)
  6. dry with materialdried over magnesium sulfate
  7. customAfter treatment with charcoal, removal of solvent
  8. customgave a cream solid, which
  9. customwas recrystallized from diethyl ether

Sources & evidence

ORD record
ord-ddbfa24994564e159e35de49eea8bc47
Source dataset
uspto-grants-2003_09
Patent number
US06624162B2

Reaction notes

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