Triethylamine → 2-Pyrrolidinone,1-(imidazo[1,2-a]pyridin-3-ylmethyl)-4-phenyl-

HRID 2043574Notes

Reaction equation

HRID 2043574 reaction equation
NC1C=CC=CN=1.BrC(C=O)C=O.[N:14]1[CH:15]=[C:16]([CH:23]=O)[N:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=12.C(N(CC)CC)C.Cl.[NH2:33][CH2:34][CH:35]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[CH2:36][C:37](OC)=[O:38]>C(O)C.O1CCOCC1>[N:14]1[CH:15]=[C:16]([CH2:23][N:33]2[CH2:34][CH:35]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH2:36][C:37]2=[O:38])[N:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=12

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 104392-AminopyridineHCID 749452-BromopropanedialHCID 10510981Imidazo[1,2-a]pyridine-3-carbaldehydeHCID 68748102Methyl 4-amino-3-phenylbutanoate hydrochloride

Product 1

HCID 159524532-Pyrrolidinone,1-(imidazo[1,2-a]pyridin-3-ylmethyl)-4-phenyl-

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-aminopyridine x8 (1 g, 1 eq, 10.6 mmol) and bromomalonaldehyde x9 (1.6 g, 1 eq, 10.6 mmol) in 1.4 dioxane (20 ml) is refluxed for 3 days (Imidazo[1,2-a]pyridine-3-carbaldehyde x10 is formed in situ and not isolated). After cooling to room temperature, triethylamine (2.96 ml, 2 eq, 21.25 mmol), methyl 4-amino-3-phenylbutanoate hydrochloride x11 (2.44 g, 1 eq, 10.6 mmol) and ethanol (10 ml) are successively added. The mixture is then allowed to react during 3 days at room temperature. The reaction mixture is poured on ice, and organic solvents are removed under reduced pressure. The resulting aqueous layer is extracted by CH2Cl2 and the cumulated organic layers are dried over MgSO4, filtered, and condensed under reduced pressure. The crude product is purified by preparative chromatography on silicagel (CH2Cl2/iPrOH: 97/3 (v/v)), then recristaltized in ethyl acetate leading to 1-(imidazo[1,2-a]pyridin-3-ylmethyl)-4-phenylpyrrolidin-2-one 7 as a white powder.

Workup

  1. customis formed in situ
  2. customnot isolated)
  3. customto react during 3 days at room temperature
  4. additionThe reaction mixture is poured on ice, and organic solvents
  5. customare removed under reduced pressure
  6. extractionThe resulting aqueous layer is extracted by CH2Cl2
  7. dry with materialthe cumulated organic layers are dried over MgSO4
  8. filtrationfiltered
  9. customcondensed under reduced pressure
  10. customThe crude product is purified by preparative chromatography on silicagel (CH2Cl2/iPrOH: 97/3 (v/v))

Sources & evidence

ORD record
ord-9180c9f91ec3418498364f944d5abb85
Source dataset
uspto-grants-2013_11
Patent number
US08586623B2

Reaction notes

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