Water → HCID 178481350, compound

HRID 1521681Notes

Reaction equation

HRID 1521681 reaction equation
C(O)(C(F)(F)F)=O.O(C1C=CC(C[N:20]2[CH:35]=[C:23]3[C:24](=[O:34])[N:25]([CH3:33])[C:26]4[N:27]([CH2:28][C:29]([CH3:32])([CH3:31])[N:30]=4)[C:22]3=[N:21]2)=CC=1)C1C=CC=CC=1.C(S(O)(=O)=O)(F)(F)F.O>C(Cl)Cl>[CH3:33][N:25]1[C:24](=[O:34])[C:23]2=[CH:35][NH:20][N:21]=[C:22]2[N:27]2[CH2:28][C:29]([CH3:32])([CH3:31])[N:30]=[C:26]12

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 90408710HCID 90408710, compound

Product 1

HCID 178481350HCID 178481350, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (600 mL) is added into a suspension of 2-(4-phenoxybenzyl)-7,8-dihydro-5,7,7-trimethyl-[2H]-imidazo-[1,2-a]pyrazolo[4,3-e]pyrimidin-4(5H)-one (103 g, 257 mmol) in methylene chloride (210 mL) to give a tan solution, and then TFMSA (168 mL) is added. The reaction mixture is stirred at room temperature until the starting material disappears. The mixture is poured into cold water (3 L). After filtration, the filter cake is washed with water twice, and then basified with ammonium hydroxide aqueous solution, followed by adding ethyl acetate with stirring. The precipitated solids are filtered, washed successively with water three times, ethyl acetate twice and methanol once, and then dried under vacuum to give 45 g of product (yield: 80%). MS (ESI) m/z 220.2 [M+H]+.

Workup

  1. customto give a tan solution
  2. filtrationAfter filtration
  3. washthe filter cake is washed with water twice
  4. additionby adding ethyl acetate
  5. stirringwith stirring
  6. filtrationThe precipitated solids are filtered
  7. washwashed successively with water three times, ethyl acetate twice
  8. dry with materialmethanol once, and then dried under vacuum

Sources & evidence

ORD record
ord-7be60d54531842fa81c45f6241f81686
Source dataset
uspto-grants-2015_07
Patent number
US09073936B2

Reaction notes

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