STK345463 → HCID 10137338, compound

HRID 2109639Notes

Reaction equation

HRID 2109639 reaction equation
Cl[C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N:27]1[CH2:31][CH2:30][CH:29]([NH2:32])[CH2:28]1>C(Cl)Cl>[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N:27]1[CH2:31][CH2:30][CH:29]([NH:32][C:2]2[C:7]([C:8]([NH:10][C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=3)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH2:28]1

Participants

4

Reactant 2

HCID 683662STK345463HCID 219594033-Pyrrolidinamine,1-(2-pyridinyl)-(9CI)

Product 1

HCID 10137338HCID 10137338, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of (2-chloro(3-pyridyl))-N-(3-trifluoromethylphenyl)carboxamide and 1-(2-pyridyl) pyrrolidine-3-ylamine (Step A) was heated at 130° C. neat for 3 h. The reaction was cooled and diluted with CH2Cl2 and washed with H2O twice followed by brine. The organic layer was dried with Na2SO4 and evaporated under reduced pressure. The residue was purified by column chromatography with EtOAc and further mixed with MeOH and 1 N HCl/Et2O (2 ml). The solution was evaporated to furnish the titled compound. MS (ES+): 428 (M+H); (ES−): 426 (M−H). Calc'd. for C22H20F3N5O−427.2.

Workup

  1. temperatureThe reaction was cooled
  2. washwashed with H2O
  3. dry with materialThe organic layer was dried with Na2SO4
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography with EtOAc
  6. additionfurther mixed with MeOH and 1 N HCl/Et2O (2 ml)
  7. customThe solution was evaporated

Sources & evidence

ORD record
ord-c068df8d7d5e4ab98f2a8d3354f25420
Source dataset
uspto-grants-2009_04
Patent number
US07514564B2

Reaction notes

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