Phosphorus oxychloride → HCID 22504366, compound

HRID 1814144Notes

Reaction equation

HRID 1814144 reaction equation
[F:1][C:2]1[C:3](=O)[NH:4][CH:5]=[N:6][C:7]=1[C:8]1[N:20]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[C:11]2=[N:12][CH:13]=[C:14]([S:16]([CH3:19])(=[O:18])=[O:17])[CH:15]=[C:10]2[CH:9]=1.P(Cl)(Cl)([Cl:32])=O>>[F:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:21][N:20]2[C:11]3=[N:12][CH:13]=[C:14]([S:16]([CH3:19])(=[O:18])=[O:17])[CH:15]=[C:10]3[CH:9]=[C:8]2[C:7]2[C:2]([F:1])=[C:3]([Cl:32])[N:4]=[CH:5][N:6]=2)=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 135719064HCID 135719064, compound

Product 1

HCID 22504366HCID 22504366, compound

Procedure

A mixture of 5-fluoro-6-(1-(4-fluorobenzyl)-5-methanesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-3H-pyrimidin-4-one obtained in Example 36 (4) (20 mg) and phosphorus oxychloride (1 ml) was heated under reflux for 3 hours. The mixture was concentrated under reduced pressure, diluted with dichloromethane, washed with water, dried and concentrated under reduced pressure. The resulting residue was separated using silica gel column chromatography (methanol:dichloromethane=1:99) to obtain the desired product (13 mg) as a white powder.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. concentrationThe mixture was concentrated under reduced pressure
  4. additiondiluted with dichloromethane
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was separated

Sources & evidence

ORD record
ord-d5468d8868d34d49898a1daaf8dc985a
Source dataset
uspto-grants-2005_04
Patent number
US06875770B2

Reaction notes

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