HCID 59262196, compound → HCID 59262173, compound

HRID 534806Notes

Reaction equation

HRID 534806 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[N:14]=[CH:13][C:12]([C:15]([N:17]([CH2:39][CH2:40][O:41][CH3:42])[C:18]3[CH:23]=[CH:22][C:21]([CH2:24][N:25]4[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[C@@H:27]([CH3:38])[CH2:26]4)=[CH:20][CH:19]=3)=[O:16])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1>Cl.O1CCOCC1.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[N:14]=[CH:13][C:12]([C:15]([N:17]([CH2:39][CH2:40][O:41][CH3:42])[C:18]3[CH:23]=[CH:22][C:21]([CH2:24][N:25]4[CH2:30][CH2:29][NH:28][C@@H:27]([CH3:38])[CH2:26]4)=[CH:20][CH:19]=3)=[O:16])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 59262196HCID 59262196, compound

Product 1

HCID 59262173HCID 59262173, compoundYield 107.2%

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

1,1-Dimethylethyl (2S)-4-[(4-{({6-[(4-fluorophenyl)oxy]-3-pyridinyl}carbonyl)[2-(methyloxy)ethyl]amino}phenyl)methyl]-2-methyl-1-piperazine carboxylate (D119) (0.077 g, 0.13 mmol) was dissolved in 4M HCl in dioxane (5 mL). A few drops of water were added and the reaction was stirred for 2 h. The solvent was removed in vacuo and the resulting yellow oil was dissolved in MeOH and loaded onto an SCX cartridge which was eluted with DCM, MeOH and 2M NH3 in MeOH. The ammoniacal fractions were combined and concentrated to give the title compound as a yellow oil (0.0667 g). MS (ES): MH+ 479.4.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe resulting yellow oil was dissolved in MeOH
  3. washwas eluted with DCM, MeOH and 2M NH3 in MeOH
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6f7687535c294e1e9c5a19f0a96aff65
Source dataset
uspto-grants-2014_10
Patent number
US08853218B2

Reaction notes

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