Sulfuric Acid → 4-(4-carbamoyl-1,2,3,6-tetrahydropyridin-1-yl)-1-(2,4-dichlorophenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridine

HRID 23547Notes

Reaction equation

HRID 23547 reaction equation
[C:1]([C:3]1[CH2:4][CH2:5][N:6]([C:9]2[CH:14]=[C:13]([CH3:15])[N:12]=[C:11]3[N:16]([C:21]4[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=4[Cl:28])[C:17]([CH3:20])=[C:18]([CH3:19])[C:10]=23)[CH2:7][CH:8]=1)#[N:2].S(=O)(=O)(O)[OH:30]>C(Cl)Cl>[C:1]([C:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[C:13]([CH3:15])[N:12]=[C:11]3[N:16]([C:21]4[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=4[Cl:28])[C:17]([CH3:20])=[C:18]([CH3:19])[C:10]=23)[CH2:5][CH:4]=1)(=[O:30])[NH2:2]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 12134656HCID 12134656, compound

Product 1

HCID 121346584-(4-carbamoyl-1,2,3,6-tetrahydropyridin-1-yl)-1-(2,4-dichlorophenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In methylene chloride (2.0 mL) was dissolved 4-(4-cyano-1,2,3,6-tetrahydropyridin-1-yl)-1-(2,4-dichlorophenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridine (0.19 g), followed by adding thereto concentrated sulfuric acid (0.5 mL) under ice-cooling, and the resulting mixture was slowly heated to room temperature and then stirred overnight. The reaction mixture was separated with ethyl acetate and a saturated aqueous sodium hydrogencarbonate solution, and the aqueous layer was extracted twice with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate and the desiccating agent was filtered off, after which the filtrate was concentrated under reduced pressure. The residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: chloroform-methanol=30:1) and the crystals precipitated were washed with ethyl acetate to obtain the title compound (0.10 g).

Workup

  1. additionby adding
  2. customThe reaction mixture was separated with ethyl acetate
  3. extractiona saturated aqueous sodium hydrogencarbonate solution, and the aqueous layer was extracted twice with ethyl acetate
  4. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  5. filtrationthe desiccating agent was filtered off
  6. concentrationafter which the filtrate was concentrated under reduced pressure
  7. customThe residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: chloroform-methanol=30:1)
  8. customthe crystals precipitated
  9. washwere washed with ethyl acetate

Sources & evidence

ORD record
ord-d46c99946b38404b8fd6648c94bb0af8
Source dataset
uspto-grants-2005_02
Patent number
US06852732B2

Reaction notes

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