Sodium Carbonate → HCID 178422653, compound

HRID 1517098Notes

Reaction equation

HRID 1517098 reaction equation
COC1C=CC(C[N:8]2[CH:12]=[C:11]([C:13]3[N:18]=[C:17]([C:19]([N:21]4[CH2:26][CH2:25][CH:24]([N:27]5[CH2:31][CH2:30][CH2:29][CH2:28]5)[CH2:23][CH2:22]4)=[O:20])[C:16]([CH3:32])=[CH:15][C:14]=3[C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([F:42])([F:41])[F:40])[CH:34]=3)[N:10]=[N:9]2)=CC=1.C([O-])([O-])=O.[Na+].[Na+]>FC(F)(F)C(O)=O>[CH3:32][C:16]1[C:17]([C:19]([N:21]2[CH2:22][CH2:23][CH:24]([N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[CH2:25][CH2:26]2)=[O:20])=[N:18][C:13]([C:11]2[N:10]=[N:9][NH:8][CH:12]=2)=[C:14]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([F:42])([F:41])[F:40])[CH:34]=2)[CH:15]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 57441141[6-[1-(4-Methoxy-benzyl)-1H-[1,2,3]triazol-4-yl]-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone2×

Product 1

HCID 178422653HCID 178422653, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

0.30 g (0.50 mmol) of [6-[1-(4-methoxy-benzyl)-1H-[1,2,3]triazol-4-yl]-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone (intermediate 13) in 3.2 ml of trifluoroacetic acid were stirred at reflux for 23 hours. The reaction mixture was then poured into crashed ice, the pH was adjusted to 8-9 with aqueous Na2CO3 and the mixture was extracted twice with CH2Cl2; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 98:2 to 4:1) to give 0.19 g (77%) of the title compound as an off-white solid. MS: 485.4 (MH+).

Workup

  1. temperatureat reflux for 23 hours
  2. additionThe reaction mixture was then poured
  3. extractionthe mixture was extracted twice with CH2Cl2
  4. washthe organic phases were washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by flash column chromatography (CH2Cl2/MeOH 98:2 to 4:1)

Sources & evidence

ORD record
ord-7108f1db531040c5b01e68b787ae87f8
Source dataset
uspto-grants-2012_07
Patent number
US08227613B2

Reaction notes

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