Dimethylformamide → HCID 117843386, compound

HRID 2209253Notes

Reaction equation

HRID 2209253 reaction equation
P(Cl)(Cl)(Cl)=O.[Br:6][C:7]1[CH:8]=[C:9]([O:16][C@@H:17]([C@H:19]2[CH2:23][N:22]([C@@H:24]([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=3)[CH3:25])[C:21](=[O:34])[CH2:20]2)[CH3:18])[C:10]2[N:11]([N:13]=[CH:14][CH:15]=2)[CH:12]=1.CN([CH:38]=[O:39])C>>[Br:6][C:7]1[CH:8]=[C:9]([O:16][C@@H:17]([C@@H:19]2[CH2:20][C:21](=[O:34])[N:22]([C@@H:24]([C:26]3[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=3)[CH3:25])[CH2:23]2)[CH3:18])[C:10]2[N:11]([N:13]=[CH:14][C:15]=2[CH:38]=[O:39])[CH:12]=1

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 117842669HCID 117842669, compound

Product 1

HCID 117843386HCID 117843386, compound

Conditions

Temperature
0 °C

Procedure

To an appropriate sized microwave vial, DMF (7.22 mL, 93.0 mmol) was added and cooled to 0° C. Phosphorus oxychloride (0.346 mL, 3.72 mmol) was slowly added and the resulting solution was stirred at room temperature for 1 h. A solution of (R)-4-((R)-1-((6-bromopyrazolo[1,5-a]pyridin-4-yl)oxy)ethyl)-1-((R)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one 6.01 (851 mg, 1.86 mmol) in DMF (3.0 mL) was then added and the solution was stirred at room temperature for 3 h. The reaction was cooled to room temperature and was slowly quenched with a saturated aqueous solution of sodium bicarbonate and the resulting mixture was stirred for 1 h at room temperature. The reaction was extracted with ethyl acetate. The combined organic layers were washed with brine, dried, filtered and concentrated under reduced pressure to isolate 6-bromo-4-((R)-1-((R)-1-((R)-1-(4-methoxyphenyl)ethyl)-5-oxopyrrolidin-3-yl)ethoxy)pyrazolo[1,5-a]pyridine-3-carbaldehyde without further purification.

Workup

  1. stirringthe solution was stirred at room temperature for 3 h
  2. temperatureThe reaction was cooled to room temperature
  3. customwas slowly quenched with a saturated aqueous solution of sodium bicarbonate
  4. stirringthe resulting mixture was stirred for 1 h at room temperature
  5. extractionThe reaction was extracted with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4db1c42747f64a2e8f00a0772b496d59
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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