Water → HCID 57742990, compound

HRID 1896480Notes

Reaction equation

HRID 1896480 reaction equation
[CH3:1]C(C)([O-])C.[K+].[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[N:13][CH:14]=2)[CH:9]=[CH:8]1.ClC[C:18]1([CH2:24][CH2:25][CH3:26])[CH2:22][NH:21][C:20](=[O:23])[CH2:19]1.O>C1COCC1>[CH2:24]([CH:18]1[CH2:22][N:21]([CH2:1][C:8]2[NH:7][C:15]3=[CH:14][N:13]=[CH:12][CH:11]=[C:10]3[CH:9]=2)[C:20](=[O:23])[CH2:19]1)[CH2:25][CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 92196-AzaindoleHCID 23665647Potassium tert-butoxideHCID 53629225HCID 53629225, compound

Product 1

HCID 57742990HCID 57742990, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium terbutoxide (522 mg, 4.65 mmol, 1.1 eq) is added to a solution of 6-azaindole x269 (500 mg, 4.23 mmol) in 4 ml of THF at 0° C. After 1 hour of reaction at 0° C., a freshly prepared solution of 4-(chloromethyl)-4-propylpyrrolidin-2-one x63 (0.814 mg, 4.65 mmol, 1.1 eq, in 3 ml of THF) at 0° C. The reaction mixture is warmed to room temperature. After 3 days of agitation, water (10 ml) is added and the aqueous layer is washed with ethyl acetate (3×15 ml). The aqueous layer is then neutralized until pH 9 and extracted with dichloromethane (3×15 ml). The cumulated dichloromethane layers are dried over MgSO4, filtrated and condensed under reduced pressure. The resulting residue is purified by preparative chromatography on silicagel (CH2Cl2/MeOH/NH4OH 96/4/0.4 (v/v/v)), recrystallized in ethyl acetate, leading to 4-propyl-1-(1H-pyrrolo[2,3-c]pyridin-2-ylmethyl)pyrrolidin-2-one 242 as a solid.

Workup

  1. customAfter 1 hour of reaction at 0° C.
  2. customat 0° C
  3. washthe aqueous layer is washed with ethyl acetate (3×15 ml)
  4. extractionextracted with dichloromethane (3×15 ml)
  5. dry with materialThe cumulated dichloromethane layers are dried over MgSO4
  6. filtrationfiltrated
  7. customcondensed under reduced pressure
  8. customThe resulting residue is purified by preparative chromatography on silicagel (CH2Cl2/MeOH/NH4OH 96/4/0.4 (v/v/v))
  9. customrecrystallized in ethyl acetate

Sources & evidence

ORD record
ord-2f88637af8e2465bad31470280a46a70
Source dataset
uspto-grants-2013_08
Patent number
US08518943B2

Reaction notes

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