Triacetoxyperiodinane → N-[[1,6-Diethyl-4-[(tetrahydro-2H-pyran-4-yl)amino]-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl]-4-(5-oxopentyl)benzamide

HRID 385269Notes

Reaction equation

HRID 385269 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH2:23]([N:25]1[C:29]2=[N:30][C:31]([CH2:57][CH3:58])=[C:32]([CH2:41][NH:42][C:43](=[O:56])[C:44]3[CH:49]=[CH:48][C:47]([CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][OH:55])=[CH:46][CH:45]=3)[C:33]([NH:34][CH:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)=[C:28]2[CH:27]=[N:26]1)[CH3:24]>C1COCC1.C(Cl)Cl>[CH2:23]([N:25]1[C:29]2=[N:30][C:31]([CH2:57][CH3:58])=[C:32]([CH2:41][NH:42][C:43](=[O:56])[C:44]3[CH:45]=[CH:46][C:47]([CH2:50][CH2:51][CH2:52][CH2:53][CH:54]=[O:55])=[CH:48][CH:49]=3)[C:33]([NH:34][CH:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)=[C:28]2[CH:27]=[N:26]1)[CH3:24]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 58505267N-[[1,6-Diethyl-4-[(tetrahydro-2H-pyran-4-yl)amino]-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl]-4-(5-hydroxypentyl)benzamide

Product 1

HCID 58505298N-[[1,6-Diethyl-4-[(tetrahydro-2H-pyran-4-yl)amino]-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl]-4-(5-oxopentyl)benzamideYield 99.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dess Martin Reagent (432 mg, 1.02 mmol) was added to a solution of Intermediate 34 (250 mg, 0.51 mmol) in THF (5 mL) and DCM (5 mL). The resultant mixture was stirred at rt for 2 h. The solvent was removed in vacuo and the crude solid was purified by column chromatography on silica gel eluting with 0-10% DCM-MeOH to afford the title compound as a white solid (250 mg). ES/MS calcd. for C28H38N5O3+ 492.3. found m/z=492.3 (M+H)+.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe crude solid was purified by column chromatography on silica gel eluting with 0-10% DCM-MeOH

Sources & evidence

ORD record
ord-f083c299a128484e9677b3284105d1b0
Source dataset
uspto-grants-2013_02
Patent number
US08367829B2

Reaction notes

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