Citric Acid → HCID 57731537, compound

HRID 2234696Notes

Reaction equation

HRID 2234696 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[CH:19]=[CH:20][C:21]([NH:29][C:30]4[CH:31]=[N:32][CH:33]=[N:34][CH:35]=4)=[C:22]([CH:28]=3)[C:23]([N:25]([CH3:27])[CH3:26])=[O:24])[CH:16]=2)[N:11](S(C2C=CC(C)=CC=2)(=O)=O)[CH:10]=1.[OH-].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[CH:19]=[CH:20][C:21]([NH:29][C:30]4[CH:31]=[N:32][CH:33]=[N:34][CH:35]=4)=[C:22]([CH:28]=3)[C:23]([N:25]([CH3:26])[CH3:27])=[O:24])[CH:16]=2)[NH:11][CH:10]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14797Potassium HydroxideHCID 57731440HCID 57731440, compound

Product 1

HCID 57731537HCID 57731537, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

67 mg (0.11 mmol) of 5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-2-(pyrimidin-5-ylamino)-benzamide was dissolved in 3 mL of hot ethanol. 200 μL of 50% w/v aqueous potassium hydroxide was added and the mixture left at ambient temperature for 4.5 h. 10% w/v aqueous citric acid was added and the mixture partitioned between dichloromethane and water. The aqueous layer was extracted three times with dichloromethane. The combined organic phases were dried over sodium sulfate and evaporated. The residue was purified by mass-triggered reverse-phase HPLC to afford 21.9 mg (47 μmol, 43%) of 5-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-2-(pyrimidin-5-ylamino)-benzamide as a beige solid. 1H-NMR (500 MHz, d6-DMSO): δ 11.91 (s, br., 1H), 8.64 (s, 1H), 8.55 (d, 1H), 8.51 (s, 2H), 8.17 (d, 1H), 8.12 (s, 1H), 7.74 (d, 1H), 7.73 (dd, 1H), 7.63-7.61 (m, 2H), 7.39 (d, 1H), 7.30 (dd(d), 1H), 7.14 (d, 1H), 7.06 (t, 1H), 3.83 (s, 3H), 2.90 (s, 3H), 2.88 (s, 3H); MS: m/z 465.0 (M+H+).

Workup

  1. additionwas added
  2. additionwas added
  3. customthe mixture partitioned between dichloromethane and water
  4. extractionThe aqueous layer was extracted three times with dichloromethane
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. customevaporated
  7. customThe residue was purified by mass-triggered reverse-phase HPLC

Sources & evidence

ORD record
ord-43fff49cf0c34dfeabebb669591c7855
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

Loading…