Water → HCID 13068199, compound

HRID 851114Notes

Reaction equation

HRID 851114 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][N:11]3[C:16]=2[CH2:17][C:18]([OH:20])=O)=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[CH3:27][N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.O>CN(C)C=O>[CH3:27][N:28]1[CH2:33][CH2:32][N:31]([C:18]([CH2:17][C:16]2[N:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]3=[N:9][C:8]=2[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[O:20])[CH2:30][CH2:29]1

Participants

6

Reactant 4

HCID 962WaterHCID 531671-MethylpiperazineHCID 65578Oxalyl chlorideHCID 87285Imidazo(1,2-a)pyridine-3-acetic acid, 2-(p-chlorophenyl)-

Product 1

HCID 13068199HCID 13068199, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

4.5 g (15.64 millimols) of 2-(4-chlorophenyl)-imidazo[1,2-a]pyridine-3-acetic acid are added to a suspension of N,N-dimethyl-chloro-methyleneiminium chloride prepared by adding 2.2 g (17.75 millimols) of oxalyl chloride to 30 ml of dimethylformamide (DMF) at -10° C. The suspension is stirred for 15 minutes at 0° C. and a solution of 5.4 g (54 millimols) of 4-methylpiperazine in 10 ml of dry DMF is then added gradually thereto at 0° C. The solution is stirred for 8 hours and then poured into 750 ml of water. The amide is extracted with CH2Cl2, the organic phase is dried over Na2SO4 and concentrated, the residue is passed through a silica column (eluant: CH2Cl2 /CH3OH 9/1) and the compound obtained is recrystallised from an isopropyl ether/acetonitrile mixture. Melting point=175° C.

Workup

  1. customprepared
  2. customat 0° C
  3. stirringThe solution is stirred for 8 hours
  4. extractionThe amide is extracted with CH2Cl2
  5. dry with materialthe organic phase is dried over Na2SO4
  6. concentrationconcentrated
  7. customthe compound obtained
  8. customis recrystallised from an isopropyl ether/acetonitrile mixture

Sources & evidence

ORD record
ord-59d1d739058b45f79e192d796c5e7939
Source dataset
uspto-grants-1983_05
Patent number
US04382938

Reaction notes

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