Potassium Hydroxide → HCID 67147507, compound

HRID 2426815Notes

Reaction equation

HRID 2426815 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[N:15]([CH2:21][CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][N:27]([CH2:30][CH2:31][OH:32])[CH2:26][CH2:25]1)[CH:14]=[C:13]2[C:33]1[N:41](S(C2C=CC(C)=CC=2)(=O)=O)[C:36]2=[N:37][CH:38]=[CH:39][CH:40]=[C:35]2[CH:34]=1.[OH-].[K+]>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[N:15]([CH2:21][CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][N:27]([CH2:30][CH2:31][OH:32])[CH2:26][CH2:25]1)[CH:14]=[C:13]2[C:33]1[NH:41][C:36]2=[N:37][CH:38]=[CH:39][CH:40]=[C:35]2[CH:34]=1

Participants

3

Reactant 2

HCID 14797Potassium HydroxideHCID 67147737HCID 67147737, compound

Product 1

HCID 67147507HCID 67147507, compoundYield 90%

Conditions

Temperature
20 °C

Procedure

A solution of 2-[4-(3-{5,6-dimethoxy-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]indol-1-yl}propyl)piperazin-1-yl]ethanol trifluoroacetate (0.038 g; 52.2 μmol) in a methanolic potassium hydroxide solution (3 ml, 0.1 g of potassium hydroxide per ml of methanol) is placed in a hemolysis tube (1.3×10 cm) and is agitated at 20° C. for 72 hours. The solid form is filtered off and then purified by reverse-phase liquid chromatography mass spectrometry (method E). The fractions containing the expected compound are combined and then evaporated under reduced pressure, giving 2-(4-{3-[5,6-dimethoxy-3-(1H-pyrrolo[2,3-b]pyridin-2-yl)indol-1-yl]propyl}piperazin-1-yl)ethanol trifluoroacetate (0.022 g; 90%), the characteristics of which are as follows:

Workup

  1. filtrationThe solid form is filtered off
  2. custompurified by reverse-phase liquid chromatography mass spectrometry (method E)
  3. additionThe fractions containing the expected compound
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b766ccc2e4734e4db427ae259d407461
Source dataset
uspto-grants-2011_06
Patent number
US07968566B2

Reaction notes

Loading…