Potassium Carbonate → HCID 12114194, compound

HRID 2121690Notes

Reaction equation

HRID 2121690 reaction equation
[NH2:1][C:2]1[N:3]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[C:4]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[CH:5][C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1O)=[O:8].CC1C=CC(S([O:39][CH2:40][C@H:41]2[O:45][C:44]([CH3:47])([CH3:46])[O:43][CH2:42]2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cl-].[Na+].O>[NH2:1][C:2]1[N:3]([C:22]2[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=2)[C:4]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[CH:5][C:6]=1[C:7]([C:9]1[CH:10]=[CH:11][CH:12]=[C:13]([O:39][CH2:40][C@H:41]2[CH2:42][O:43][C:44]([CH3:46])([CH3:47])[O:45]2)[CH:14]=1)=[O:8]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2723760(S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-ToluenesulfonateHCID 23434148HCID 23434148, compound

Product 1

HCID 12114194HCID 12114194, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 0.6 g (1.6 mmol) of [2-amino-1-(4-fluorophenyl)-5-pyridin-3-yl-1H-pyrrol-3-yl](hydroxyphenyl)methanone, 1.06 g (3.7 mmol) of L-α,β-isopropylideneglycerol-γ-tosylate and 1.2 g (8.7 mmol) of potassium carbonate in 10 mL of DMF was heated at 80°. After 16 h, the reaction mixture was cooled to room temperature, poured into brine and extracted with ethyl acetate. The extracts were dried over sodium sulfate, concentrated under reduced pressure and purified by flash chromatography (gradient elution: 15-50% ethyl acetate/hexane) to give 0.7 g (90%) of [2-amino-1-(4-fluorophenyl)-5-pyridin-3-yl-1H-pyrrol-3-yl]-[3-(2,2-dimethyl-[1,3 ]dioxolan-4(S)-ylmethoxy)-phenyl]-methanone.

Workup

  1. temperaturewas heated at 80°
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extracts were dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. custompurified by flash chromatography (gradient elution: 15-50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a49c8f5093b740dca7eb0564b2536f3e
Source dataset
uspto-grants-2004_02
Patent number
US06696471B2

Reaction notes

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