Phosphorus oxychloride → HCID 53237746, compound

HRID 1187310Notes

Reaction equation

HRID 1187310 reaction equation
[F:1][C:2]1[C:7]([C:8]([C:10]2[C:18]3[C:17](O)=[N:16][CH:15]=[N:14][C:13]=3[NH:12][CH:11]=2)=[O:9])=[C:6]([F:20])[CH:5]=[CH:4][C:3]=1[NH:21][S:22]([C:25]1[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][CH3:33])=[CH:27][CH:26]=1)(=[O:24])=[O:23].P(Cl)(Cl)([Cl:36])=O>>[Cl:36][C:17]1[C:18]2[C:10]([C:8]([C:7]3[C:2]([F:1])=[C:3]([NH:21][S:22]([C:25]4[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][CH3:33])=[CH:27][CH:26]=4)(=[O:24])=[O:23])[CH:4]=[CH:5][C:6]=3[F:20])=[O:9])=[CH:11][NH:12][C:13]=2[N:14]=[CH:15][N:16]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178439340HCID 178439340, compound

Product 1

HCID 53237746HCID 53237746, compoundYield 87.8%

Conditions

Temperature
100 °C

Procedure

To N-[2,4-difluoro-3-(4-hydroxy-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-phenyl]-4-propyl-benzenesulfonamide (P-1030, 239 mg, 0.506 mmol), phosphoryl chloride (4.0 mL, 43 mmol) is added and the suspension is heated in an oil bath at 100° C. for one hour. The reaction is allowed to cool, then poured onto ice. The resulting solid is collected by vacuum filtration and dried to provide the desired compound (P-1030, 218 mg). MS (ESI) [M+H+]+=490.9.

Workup

  1. temperatureto cool
  2. additionpoured onto ice
  3. filtrationThe resulting solid is collected by vacuum filtration
  4. customdried

Sources & evidence

ORD record
ord-7a894be550f34a4b9619c171183b4872
Source dataset
uspto-grants-2014_03
Patent number
US08673928B2

Reaction notes

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