Water → HCID 66998229, compound

HRID 559260Notes

Reaction equation

HRID 559260 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:29](=[O:30])[N:28]([CH3:31])[C:12]2[N:13]([CH3:27])[C:14]3[C:19]([C:11]=2[CH:10]=1)=[CH:18][C:17]([C:20]1[N:21]=[C:22]([CH2:25]O)[S:23][CH:24]=1)=[CH:16][CH:15]=3.C(N(S(F)(F)[F:38])CC)C.O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:29](=[O:30])[N:28]([CH3:31])[C:12]2[N:13]([CH3:27])[C:14]3[C:19]([C:11]=2[CH:10]=1)=[CH:18][C:17]([C:20]1[N:21]=[C:22]([CH2:25][F:38])[S:23][CH:24]=1)=[CH:16][CH:15]=3

Participants

5

Reactant 3

HCID 962WaterHCID 123472(Diethylamino)sulfur trifluoride2×HCID 66998274HCID 66998274, compound

Product 1

HCID 66998229HCID 66998229, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

150 mg (0.319 mmol) of compound from Example 9, 3-(2,4-dichlorophenyl)-6-(2-hydroxymethylthiazol-4-yl)-1,9-dimethyl-1,9-dihydropyrido[2,3-b]indol-2-one, are dissolved in 3 ml of CH2Cl2. 51 μl of (diethylamino)sulphur trifluoride (DAST) are added at 0° C. The mixture is stirred at 0° C. for 2 hours. A further 100 μl of DAST are added (presence of starting product) and the mixture is left to stir at ambient temperature for a further 16 hours. H2O is added, the mixture is extracted with CH2Cl2, and the organic phase is dried over MgSO4, filtered and concentrated to dryness, adsorbing onto silica. Purification is carried out on a silica column, elution being carried out with EtOAc/40% cyclohexane and then with EtOAc/30% cyclohexane. The residue is taken up in MeOH and the precipitate is filtered off, and washed with MeOH and then with a minimum amount of Et2O.

Workup

  1. waitthe mixture is left
  2. stirringto stir at ambient temperature for a further 16 hours
  3. extractionthe mixture is extracted with CH2Cl2
  4. dry with materialthe organic phase is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customPurification
  8. washis carried out on a silica column, elution
  9. filtrationthe precipitate is filtered off
  10. washwashed with MeOH

Sources & evidence

ORD record
ord-f9fb24ae64b24c959aeb3a882e784ae1
Source dataset
uspto-grants-2011_11
Patent number
US08063061B2

Reaction notes

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