Water → HCID 86606161, compound

HRID 269785Notes

Reaction equation

HRID 269785 reaction equation
[CH3:1][C:2](=[N:4]O)[CH3:3].[H-].[Na+].[Cl:8][C:9]1[N:14]=[C:13](S(C)(=O)=O)[N:12]=[C:11]([NH:19][C@H:20]([C:22]([F:25])([F:24])[F:23])[CH3:21])[C:10]=1[C:26]1[C:31]([F:32])=[CH:30][C:29]([F:33])=[CH:28][C:27]=1[F:34].O.C[N:37](C)C=O>>[Cl:8][C:9]1[N:14]=[C:13]([NH:37][N:4]=[C:2]([CH3:3])[CH3:1])[N:12]=[C:11]([NH:19][C@H:20]([C:22]([F:25])([F:24])[F:23])[CH3:21])[C:10]=1[C:26]1[C:31]([F:32])=[CH:30][C:29]([F:33])=[CH:28][C:27]=1[F:34]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 67180Acetone, oximeHCID 11327963HCID 11327963, compound

Product 1

HCID 86606161HCID 86606161, compound

Conditions

Temperature
22.5 °C

Procedure

0.16 g (2.2 mmol) of acetone oxime was added to 0.065 g (2.4 mmol) of sodium hydride in 10 ml of dimethylformamide (DMF). The mixture was stirred at 20-25° C. for 1 hour, after which 1.0 g (2.2 mmol) of [6-chloro-2-methanesulfonyl-5-(2,4,6-trifluorophenyl)pyrimidin-4-yl]-((S)-1-trifluoromethylethyl)amine (abbr. sulfone 1) was added. After a further 14 hours of stirring at 20-25° C., the mixture was poured into water and extracted with dichloromethane. The combined organic phases were washed with water, then dried and finally freed from the solvent. This gave 0.6 g of the title compound of m.p. 157-159° C.

Workup

  1. stirringAfter a further 14 hours of stirring at 20-25° C.
  2. extractionextracted with dichloromethane
  3. washThe combined organic phases were washed with water
  4. customdried

Sources & evidence

ORD record
ord-cf4b52e526e04593a4f3a717c1d337ba
Source dataset
uspto-grants-2008_11
Patent number
US07449471B2

Reaction notes

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