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

HRID 1171097
Notes
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Reaction equation

HRID 1171097 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 AcidSolvent
HCID 24247
Perchloric Acid
Solvent

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-6c0d1913ba6446c59afc77b66225a7c1
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07829558B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes