Hydrochloric Acid → HCID 68621990, compound

HRID 2113472Notes

Reaction equation

HRID 2113472 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:22]3[C:17](=[CH:18][C:19]([C:23]([N:25]4[CH2:30][CH2:29][N:28]([CH:31]([CH3:33])[CH3:32])[CH2:27][CH2:26]4)=[O:24])=[CH:20][CH:21]=3)[CH:16]=[CH:15]2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.O1CCO[CH2:37][CH2:36]1>>[CH:31]([N:28]1[CH2:27][CH2:26][N:25]([C:23]([C:19]2[CH:20]=[C:21]3[C:22](=[CH:17][CH:18]=2)[N:14]([CH:11]2[CH2:12][CH2:13][N:8]([CH2:6][CH2:36][CH3:37])[CH2:9][CH2:10]2)[CH:15]=[CH:16]3)=[O:24])[CH2:30][CH2:29]1)([CH3:33])[CH3:32]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 68624858HCID 68624858, compound

Product 1

HCID 68621990HCID 68621990, compound

Conditions

Temperature
60 °C

Procedure

4-[5-(4-isopropyl-piperazine-1-carbonyl)-indol-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (example 26) was treated with 4N HCl in dioxane and evaporated to dryness. The residue was used in the consecutive step without further purification. The residue was dissolved in THF and treated with KOtBu. Propyliodide was added and heated to 60° C. After evaporation to dryness the residue was dissolved in methanol/DMF and subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile/water/NEt3. The combined product fractions were evaporated to the title compound. MS (m/e): 397.3 (MH+).

Workup

  1. customevaporated to dryness
  2. customThe residue was used in the consecutive step without further purification
  3. dissolutionThe residue was dissolved in THF
  4. additiontreated with KOtBu
  5. additionPropyliodide was added
  6. customAfter evaporation to dryness the residue
  7. dissolutionwas dissolved in methanol/DMF
  8. customsubjected to purification by preparative HPLC on reversed phase
  9. washeluting with a gradient
  10. customformed from acetonitrile/water/NEt3
  11. customThe combined product fractions were evaporated to the title compound

Sources & evidence

ORD record
ord-69ae84de76544b3fa8fd546b8e864736
Source dataset
uspto-grants-2008_10
Patent number
US07432255B2

Reaction notes

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