Methylamine → HCID 21922747, compound

HRID 1245015Notes

Reaction equation

HRID 1245015 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)=[C:15]2[C:26]2[CH:31]=[CH:30][N:29]=[C:28](F)[CH:27]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:33][NH2:34]>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH:18]=[CH:17][C:16]([C:19]3[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=3)=[C:15]2[C:26]2[CH:31]=[CH:30][N:29]=[C:28]([NH:34][CH3:33])[CH:27]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 21922798HCID 21922798, compound

Product 1

HCID 21922747HCID 21922747, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
150 °C

Procedure

A mixture of a solution of 1.50 g (3.49 mmol) of 1-(1-benzylpiperidin-4-yl)-3-(4-fluorophenyl)-2-(2-fluoropyridin-4-yl)-1H-pyrrole [prepared as described in step 72(i) above] in 30 ml of tetrahydrofuran and 50 ml (100 mmol) of a 2M solution of methylamine in tetrahydrofuran was stirred at 150° C. in an autoclave for 28 hours. At the end of this time, the solvent was distilled off from the reaction mixture under reduced pressure. Ethyl acetate and water were added to the residue, and the organic layer was separated, dried over anhydrous magnesium sulfate and then concentrated by evaporation under reduced pressure. The residue thus obtained was purified by chromatography on a silica gel column using a 20:1 by volume mixture of dichloromethane and methanol as the eluant to give 1.83 g (yield 60%) of the title compound as a pale brown amorphous solid.

Workup

  1. distillationAt the end of this time, the solvent was distilled off from the reaction mixture under reduced pressure
  2. additionEthyl acetate and water were added to the residue
  3. customthe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by chromatography on a silica gel column
  8. additionby volume mixture of dichloromethane and methanol as the eluant

Sources & evidence

ORD record
ord-c985eb8170b942308e9ffdfb6829c803
Source dataset
uspto-grants-2006_10
Patent number
US07122666B2

Reaction notes

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