Potassium Hydroxide → HCID 68513183, compound

HRID 549055Notes

Reaction equation

HRID 549055 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:8][CH:9]=2)[C:4]([C:19]2[N:27](S(C3C=CC(C)=CC=3)(=O)=O)[C:22]3=[N:23][CH:24]=[CH:25][CH:26]=[C:21]3[CH:20]=2)=[CH:3]1.[OH-].[K+]>CO>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:15])[CH3:16])=[CH:8][CH:9]=2)[C:4]([C:19]2[NH:27][C:22]3=[N:23][CH:24]=[CH:25][CH:26]=[C:21]3[CH:20]=2)=[CH:3]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 68512630HCID 68512630, compound

Product 1

HCID 68513183HCID 68513183, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of {1-methyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-1H-indol-5-yl}-carbamic acid, tert-butyl ester [0.3 g, Reference Example 13(f)] in methanol (15 mL) was treated with potassium hydroxide solution (5N, 2 mL) then heated at reflux for 4 hours. The reaction mixture was evaporated and the residue triturated with water to give the title compound (0.2 g) as a tan solid. MS: 263 (MH+). TLC: RF=0.3 (ethyl acetate).

Workup

  1. temperaturethen heated
  2. temperatureat reflux for 4 hours
  3. customThe reaction mixture was evaporated
  4. customthe residue triturated with water

Sources & evidence

ORD record
ord-0f75cb9b08984b0098de5ebfa56b4071
Source dataset
uspto-grants-2011_05
Patent number
US07943616B2

Reaction notes

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