Potassium Carbonate → HCID 58930969, compound

HRID 387935Notes

Reaction equation

HRID 387935 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[NH:41][C:18]3[N:19]=[CH:20][N:21]=[C:22]([O:23][C:24]4[CH:29]=[CH:28][C:27]([NH:30][C:31]([NH:33][C:34]5[CH:39]=[CH:38][CH:37]=[C:36]([F:40])[CH:35]=5)=[O:32])=[CH:26][CH:25]=4)[C:17]=3[CH:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C.O1CCCC1>FC(F)(F)C(O)=O.C1(SC)C=CC=CC=1>[F:40][C:36]1[CH:35]=[C:34]([NH:33][C:31]([NH:30][C:27]2[CH:26]=[CH:25][C:24]([O:23][C:22]3[C:17]4[CH:16]=[C:15]([C:12]5[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=5)[NH:41][C:18]=4[N:19]=[CH:20][N:21]=3)=[CH:29][CH:28]=2)=[O:32])[CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 21939870Tetrahydrofuran ethyl acetateHCID 58930883HCID 58930883, compound

Product 1

HCID 58930969HCID 58930969, compoundYield 98.5%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7520ThioanisoleSolvent

Conditions

Temperature
45 °C

Procedure

After dissolving 377 mg of 1-{4-[6-(4-benzyloxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy]phenyl}-3-(3-fluorophenyl)urea in 4 ml of trifluoroacetic acid and 0.4 ml of thioanisole, the solution was stirred at 45° C. for 40 minutes. It was then returned to room temperature, potassium carbonate was added to alkalinity, and liquid separation and extraction were performed with an ethyl acetate-tetrahydrofuran (5:1) mixed solvent. The organic layer was concentrated to dryness to obtain 310 mg of the title compound.

Workup

  1. customwas then returned to room temperature
  2. additionmixed solvent
  3. concentrationThe organic layer was concentrated to dryness

Sources & evidence

ORD record
ord-25cc0eac7e644d9da684bb37d0330bf0
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

Loading…