Hydrochloric Acid → (7-{5-[1-(4-Fluoro-phenyl)-vinyl]-[1,2,3]triazol-1-yl}-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)-acetic acid

HRID 570666Notes

Reaction equation

HRID 570666 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[N:15]([CH:16]3[CH2:32][N:20]4[C:21]5[C:26]([C:27]([CH2:28][C:29]([OH:31])=[O:30])=[C:19]4[CH2:18][CH2:17]3)=[CH:25][CH:24]=[CH:23][CH:22]=5)[N:14]=[N:13][CH:12]=2)(O)[CH3:9])=[CH:4][CH:3]=1.Cl>O1CCOCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[N:15]([CH:16]3[CH2:32][N:20]4[C:21]5[C:26]([C:27]([CH2:28][C:29]([OH:31])=[O:30])=[C:19]4[CH2:18][CH2:17]3)=[CH:25][CH:24]=[CH:23][CH:22]=5)[N:14]=[N:13][CH:12]=2)=[CH2:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 46893925(7-{5-[1-(4-Fluoro-phenyl)-1-hydroxy-ethyl]-[1,2,3]triazol-1-yl}-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)-acetic acid

Product 1

HCID 46892775(7-{5-[1-(4-Fluoro-phenyl)-vinyl]-[1,2,3]triazol-1-yl}-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)-acetic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The title compound was prepared from refluxing a solution of (7-{5-[1-(4-Fluoro-phenyl)-1-hydroxy-ethyl]-[1,2,3]triazol-1-yl}-6,7,8,9-tetrahydropyrido[1,2-α]indol-10-yl)-acetic acid (EXAMPLE 5) in a 1:1 mixture of Dioxane: 2M HCl for 24 h. The reaction mixture was cooled to room temperature then extracted with EA, washed with brine, dried over Na2SO4 and evaporated. Purification by Combi-flash EA/Hex 50-100% afforded the desired compound. MS (+ESI) m/z: 417.1.

Workup

  1. customThe title compound was prepared
  2. extractionthen extracted with EA
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customPurification by Combi-flash EA/Hex 50-100%

Sources & evidence

ORD record
ord-31fccac871aa4013ac3ba0b21d69636b
Source dataset
uspto-grants-2015_05
Patent number
US09023864B2

Reaction notes

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