Potassium Hydroxide → [7-(4-Benzyl-[1,2,3]triazol-1-yl)-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]-acetic acid

HRID 1944017Notes

Reaction equation

HRID 1944017 reaction equation
[CH2:1]([C:8]1[N:9]=[N:10][N:11]([CH:13]2[CH2:32][N:17]3[C:18]4[C:23]([C:24]([CH2:25][C:26]([O:28]CCC)=[O:27])=[C:16]3[CH2:15][CH2:14]2)=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>C1COCC1.CO>[CH2:1]([C:8]1[N:9]=[N:10][N:11]([CH:13]2[CH2:32][N:17]3[C:18]4[C:23]([C:24]([CH2:25][C:26]([OH:28])=[O:27])=[C:16]3[CH2:15][CH2:14]2)=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86645391Propyl [7-(4-benzyl-1H-1,2,3-triazol-1-yl)-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]acetate

Product 1

HCID 46893800[7-(4-Benzyl-[1,2,3]triazol-1-yl)-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]-acetic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a stirred solution of propyl [7-(4-benzyl-1H-1,2,3-triazol-1-yl)-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]acetate (1 eq) in THF/MeOH (2:1, 0.1M) at room temperature was added a 2M solution of potassium hydroxide (10 eq) The reaction mixture was stirred at room temperature for 2 h then quenched by adding HCl 10% until acidic pH and diluted with dichloromethane (DCM). Filtration through a phase separator followed by evaporation afforded the desired product as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 12.13 (s, 1H), 8.05 (s, 1H), 7.46 (d, 1H), 7.40 (d, 1H), 7.34-7.17 (m, 5H), 7.12-7.00 (m, 2H), 5.35-5.18 (m, 1H), 4.67 (dd, 1H), 4.32 (dd, 1H), 4.02 (s, 2H), 3.69-3.50 (m, 2H), 3.07-2.92 (m, 2H), 2.52-2.30 (m, 2H). MS (+ESI) m/z: 387.2.

Workup

  1. customthen quenched
  2. additionby adding HCl 10% until acidic pH
  3. additiondiluted with dichloromethane (DCM)
  4. filtrationFiltration through a phase separator
  5. customfollowed by evaporation

Sources & evidence

ORD record
ord-c87a368c6ed04948960bce87e7bc5901
Source dataset
uspto-grants-2013_03
Patent number
US08394819B2

Reaction notes

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