Piperazine → HCID 89544968, compound

HRID 2283444Notes

Reaction equation

HRID 2283444 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:11][CH:12]=O)[CH2:9][CH3:10])=[C:4]([F:14])[C:3]=1[C:15]([C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)=[O:16].N1CCNCC1>C1COCC1>[Cl:1][C:2]1[C:3]([CH:15]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[OH:16])=[C:4]([F:14])[C:5]([C@H:8]([NH:11][CH3:12])[CH2:9][CH3:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 89544839HCID 89544839, compound

Product 1

HCID 89544968HCID 89544968, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

Step 2 To a stirred solution of N-[(1R)-1-{4-chloro-2-fluoro-3-[(pyridin-3-yl)carbonyl]phenyl}propyl]formamide (0.128 g, 0.399 mmol) in THF (2 mL) at room temperature was added BH3 in THF (1 M soln, 0.998 mL, 0.998 mmol) dropwise. The mixture was stirred at 50° C. overnight before it was quenched at 0° C. by the addition of excess MeOH followed by piperazine (0.352 g, 4.09 mmol). The mixture was stirred at room temperature for 1 hour before the solvents were removed under vacuum. The residue was taken into EtOAc, washed with water (×2), brine, dried (Na2SO4), filtered and concentrated providing {6-chloro-2-fluoro-3-[(1R)-1-(methylamino)propyl]-phenyl}(pyridin-3-yl)methanol which was used without further purification, 0.123 g, 100%. MS: [M+H]+ 309.

Workup

  1. customwas quenched at 0° C. by the addition of excess MeOH
  2. stirringThe mixture was stirred at room temperature for 1 hour before the solvents
  3. customwere removed under vacuum
  4. washwashed with water (×2), brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5a9a826ce21b44f0b61c73e000a895fa
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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