Potassium Carbonate → HCID 59362582, compound

HRID 1625456Notes

Reaction equation

HRID 1625456 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([C:19]4[S:20][CH:21]=[CH:22][CH:23]=4)[CH:18]=[C:13]3[C:12]([C:24]3[CH:25]=[C:26]([CH:47]=[CH:48][CH:49]=3)[CH2:27][NH:28][C:29]([C:31]3[C:32](=[O:46])[N:33]([CH2:37][C:38]4[CH:43]=[CH:42][C:41]([F:44])=[C:40]([F:45])[CH:39]=4)[CH:34]=[CH:35][CH:36]=3)=[O:30])=[CH:11]2)(=O)=O)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO.O>[S:20]1[CH:21]=[CH:22][CH:23]=[C:19]1[C:17]1[CH:18]=[C:13]2[C:12]([C:24]3[CH:25]=[C:26]([CH:47]=[CH:48][CH:49]=3)[CH2:27][NH:28][C:29]([C:31]3[C:32](=[O:46])[N:33]([CH2:37][C:38]4[CH:43]=[CH:42][C:41]([F:44])=[C:40]([F:45])[CH:39]=4)[CH:34]=[CH:35][CH:36]=3)=[O:30])=[CH:11][NH:10][C:14]2=[N:15][CH:16]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 59362475HCID 59362475, compound

Product 1

HCID 59362582HCID 59362582, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1-(3,4-Difluoro-benzyl)-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid 3-(1-benzenesulfonyl-5-thiophen-2-yl-1H-pyrrolo[2,3-b]pyridin-3-yl)-benzylamide (0.079 mmol, 0.000079 mol) was dissolved in methanol (1.8 mL, Fisher;) and water (0.60 mL, Fisher). To this was added potassium carbonate (46 mg, 0.00033 mol; Fisher) and the reaction was heated at reflux for 1 hour. The reaction was evaporated, taken up in N,N-dimethylformamide, neutralized with TFA (100 uL) and purified by preparative HPLC chromatography to yield the product in 3.4 mg yield. 1H NMR (500 MHz, CDCl3-MeOH-d4) d ppm 10.244 (s, 1H) 8.734 (s, 1H) 8.550-8.480 (m, 2H) 7.677 (s, 1H) 7.604 (s, 1H) 7.537 (s, 1H) 7.506-7.393 (m, 3H) 7.390-7.326 (m, 2H) 7.144-7.035 (m, 3H) 6.999-6.938 (m, 1H) 6.442 (m, 1H) 5.070 (s, 2H) 4.689 (m, 2H); MS m/z=552.95 M+H.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 1 hour
  3. customThe reaction was evaporated
  4. custompurified by preparative HPLC chromatography
  5. customto yield the product in 3.4 mg
  6. customyield

Sources & evidence

ORD record
ord-8116515340064ce288abd5e60828b874
Source dataset
uspto-grants-2014_07
Patent number
US08778977B2

Reaction notes

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