HCID 131730318, compound → HCID 131730319, compound

HRID 1948313Notes

Reaction equation

HRID 1948313 reaction equation
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][C@H:13]1[CH2:25][O:26][CH3:27])=[O:10]>Cl.O1CCOCC1.CO>[ClH:1].[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][NH:15][CH2:14][C@H:13]1[CH2:25][O:26][CH3:27])=[O:10]

Participants

5

Reactant 1

HCID 131730318HCID 131730318, compound2×

Product 1

HCID 131730319HCID 131730319, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

Cis(±)tert-butyl 4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-(methoxymethyl)piperidine-1-carboxylate (Intermediate 73; 192 mg, 0.45 mmol) was dissolved in 4N HCl in dioxane (10 ml) and 10 ml of MeOH. The mixture was stirred at room temperature for 3 h, concentrated to dryness and azeotroped with MeOH to remove excess HCl (5×20 ml) to yield the title compound which was used without purification. (crude mixture 195 mg). MS (ES)(MH+): 320 for C13H19Cl2N3O2.

Workup

  1. concentrationconcentrated to dryness
  2. customazeotroped with MeOH
  3. customto remove excess HCl (5×20 ml)

Sources & evidence

ORD record
ord-cee9699e3b3c45749fbf5179893f87c4
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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