HCID 59242665, compound → HCID 59242672, compound

HRID 1630476Notes

Reaction equation

HRID 1630476 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:15]=[N:16][C:17]([C:25]([F:28])([F:27])[F:26])=[C:18]([C:20]3[CH:24]=[CH:23][S:22][CH:21]=3)[CH:19]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(OC(N1CCN(C2N=NC(C(F)(F)F)=C(C3C=CC(F)=CC=3)C=2)CC1)=O)(C)(C)C>CO>[N:11]1([C:14]2[N:15]=[N:16][C:17]([C:25]([F:27])([F:26])[F:28])=[C:18]([C:20]3[CH:24]=[CH:23][S:22][CH:21]=3)[CH:19]=2)[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 59242665HCID 59242665, compoundHCID 68457855HCID 68457855, compound

Product 1

HCID 59242672HCID 59242672, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-[5-(3-thienyl)-6-trifluoromethyl-pyridazin-3-yl]-piperazine-1-carboxylic acid tert-butyl ester (0.074 g, 0.18 mmol), prepared by procedures similar to those described for D8, in methanol (5 ml) was added Amberlyst® 15 ion exchange resin, acidic form (4.1 mmol/g) (0.218 g, 0.89 mmol) and the reaction mixture was shaken at room temperature for 18 h. After this period, the mixture was filtered and then a saturated solution of ammonia in methanol was added. The mixture was shaken for 1 h, filtered and the filtrate evaporated in vacuo. The crude product was crystallized from ether/heptane to yield E7 (0.049 g, 87%). C13H13F3N4S requires 314; Found 315 (MH+).

Workup

  1. additionwas added Amberlyst® 15 ion exchange resin, acidic form (4.1 mmol/g) (0.218 g, 0.89 mmol)
  2. waitAfter this period
  3. filtrationthe mixture was filtered
  4. additiona saturated solution of ammonia in methanol was added
  5. stirringThe mixture was shaken for 1 h
  6. filtrationfiltered
  7. customthe filtrate evaporated in vacuo
  8. customThe crude product was crystallized from ether/heptane

Sources & evidence

ORD record
ord-4da3f72e77794a34bf96a206005496fd
Source dataset
uspto-grants-2014_07
Patent number
US08791120B2

Reaction notes

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