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Gamma-Butyrolactone → HCID 178520695, compound

HRID 45862
Notes
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Reaction equation

HRID 45862 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[C:9]([C:13]3[CH:14]=[C:15]([NH:19][C:20]([NH:22][C:23]4[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=4)=[O:21])[CH:16]=[CH:17][CH:18]=3)=[N:10][NH:11][CH:12]=2)[CH:5]=[CH:4][N:3]=1.[C:33]1(=[O:38])[O:37][CH2:36][CH2:35][CH2:34]1.[Na].C[Si](C)(C)N[Si](C)(C)C>O1CCCC1>[OH:38][CH2:33][CH2:34][CH2:35][C:36]([NH:1][C:2]1[CH:7]=[C:6]([C:8]2[C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([NH:19][C:20](=[O:21])[NH:22][C:23]4[CH:28]=[CH:27][C:26]([C:29]([F:31])([F:32])[F:30])=[CH:25][CH:24]=4)[CH:14]=3)=[N:10][NH:11][CH:12]=2)[CH:5]=[CH:4][N:3]=1)=[O:37]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7302Gamma-ButyrolactoneHCID 45051731Sodium hexamethyidisilazaneHCID 178507322HCID 178507322, compound

Product 1

HCID 178520695HCID 178520695, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

30 mg (0.068 mmol) of 1-{3-[4-(2-aminopyridin-4-yl)-1H-pyrazol-3-yl]phenyl}-3-[4-(trifluoromethyl)phenyl]urea were dissolved in 2 ml of dry tetrahydrofuran and 15 μl (0.34 mmol) of γ-butyrolactone were added. The reaction mixture was cooled to 0° C. and a solution of 680 μl (0.68 mmol) of hexamethyldisilazane sodium salt 1M in THF in 2 ml of the same solvent were added dropwise. The mixture was maintained at 0° C. for 6 hours and at room temperature overnight, then partitioned between dichloromethane and water. The organic phase was dried over sodium sulphate and evaporated. The crude was finally purified by preparative HPLC in reverse phase conditions (basic eluant), giving 20 mg (59%) of the title compound.

Workup

  1. temperatureThe mixture was maintained at 0° C. for 6 hours and at room temperature overnight
  2. custompartitioned between dichloromethane and water
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. customevaporated
  5. customThe crude was finally purified by preparative HPLC in reverse phase conditions (basic eluant)

Sources & evidence

ORD record
ord-3cff4afe910941b08835c59a82d566ad
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08541575B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes