Sodium Bicarbonate → N,N-dimethyl-3-(5-(3-(morpholine-4-carbonyl)phenyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)benzamide

HRID 2388923Notes

Reaction equation

HRID 2388923 reaction equation
[CH3:1][N:2]([CH3:42])[C:3](=[O:41])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([N:27]5[CH2:32][CH2:31][O:30][CH2:29][CH2:28]5)=[O:26])[CH:20]=4)[CH:17]=3)[N:12](COCC[Si](C)(C)C)[N:11]=2)[CH:5]=1.C(=O)(O)[O-].[Na+]>Cl(O)(=O)(=O)=O.C(O)(=O)C>[CH3:1][N:2]([CH3:42])[C:3](=[O:41])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([N:27]5[CH2:28][CH2:29][O:30][CH2:31][CH2:32]5)=[O:26])[CH:20]=4)[CH:17]=3)[NH:12][N:11]=2)[CH:5]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 59836180N,N-dimethyl-3-(5-(3-(morpholine-4-carbonyl)phenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)benzamide

Product 1

HCID 178484436N,N-dimethyl-3-(5-(3-(morpholine-4-carbonyl)phenyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)benzamideYield 18%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 24247Perchloric AcidSolvent

Procedure

A solution of N,N-dimethyl-3-(5-(3-(morpholine-4-carbonyl)phenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)benzamide in 5% of perchloric acid in acetic acid (1 mL) was stirred for 1 h at room temperature. Saturated sodium bicarbonate solution was then added to the solution slowly until pH 8 and the mixture was stirred for 24 hours at room temperature. Ethyl acetate was then used for extraction and the organic layers were combined, dried over sodium sulfate, filtered and concentrated to dryness. Mass triggered reverse phase HPLC purification afforded N,N-dimethyl-3-(5-(3-(morpholine-4-carbonyl)phenyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)benzamide (7.4 mg, 18% yield over two steps) as light yellow solids. 1H NMR (500 MHz, CDCl3) δ 2.99 (s, 3H), 3.10 (s, 3H), 3.46 (br, 2H), 3.61 (br, 2H), 3.76 (br, 4H), 7.40 (d, J=7.0 Hz, 1H), 7.47 (d, J=8.0 Hz, 1H), 7.52 (m, 2H), 7.64 (d, J=7.5 Hz, 1H), 7.68 (s, 1H), 7.98 (m, 2H), 8.62 (s, 1H), 8.85 (br, 1H). MS: m/z 456.1 (M+H+).

Workup

  1. extractionEthyl acetate was then used for extraction
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customphase HPLC purification

Sources & evidence

ORD record
ord-ca64316658974a8d916c4a8c08a54638
Source dataset
uspto-grants-2012_09
Patent number
US08268994B2

Reaction notes

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