Acetic Acid → N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-N'-{[6-(methyloxy)-3'-(1-piperazinylmethyl)-3-biphenylyl]methyl}-2,6-pyridinedicarboxamide

HRID 662131Notes

Reaction equation

HRID 662131 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:49][CH3:50])=[C:10]([CH2:19][NH:20][C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([NH:31][CH2:32][C:33]4[CH:34]=[C:35]([C:41]5[CH:46]=[CH:45][CH:44]=[C:43]([CH:47]=O)[CH:42]=5)[C:36]([O:39][CH3:40])=[CH:37][CH:38]=4)=[O:30])[N:24]=3)=[O:22])[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2].[NH:51]1[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]1.C(O)(=O)C>CS(C)=O>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:49][CH3:50])=[C:10]([CH2:19][NH:20][C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([NH:31][CH2:32][C:33]4[CH:34]=[C:35]([C:41]5[CH:46]=[CH:45][CH:44]=[C:43]([CH2:47][N:51]6[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]6)[CH:42]=5)[C:36]([O:39][CH3:40])=[CH:37][CH:38]=4)=[O:30])[N:24]=3)=[O:22])[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4837PiperazineHCID 57819390N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-N'-{[3'-formyl-6-(methyloxy)-3-biphenylyl]methyl}-2,6-pyridinedicarboxamide

Product 1

HCID 44192573N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-N'-{[6-(methyloxy)-3'-(1-piperazinylmethyl)-3-biphenylyl]methyl}-2,6-pyridinedicarboxamideYield 18.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

N-{[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-N′-{[3′-formyl-6-(methyloxy)-3-biphenylyl]methyl}-2,6-pyridinedicarboxamide (40.0 mg. 0.059 mmol) was diluted in DMSO (1.5 mL) and dispensed into a 1 dram vial containing piperazine (0.178 mmol) and acetic acid (0.059 mmol, 3.55 mg) and with fitted magnetic stir bar. The resulting solution was stirred at room temperature for 4 h. MP-B(OAc)3H (0.592 mmol, 138 mg) was added and the solution was stirred for another 12 h. The polymer reagent was filtered off and purification was completed via a Gilson HPLC (basic conditions) to afford 8.32 mg of the title compound (18.9%). LC-MS m/z 746 (M+H)+, 1.27 min (ret time).

Workup

  1. customwith fitted magnetic stir bar
  2. stirringthe solution was stirred for another 12 h
  3. filtrationThe polymer reagent was filtered off
  4. custompurification

Sources & evidence

ORD record
ord-2db4ff735f1141229b65606cc8352647
Source dataset
uspto-grants-2011_12
Patent number
US08084449B2

Reaction notes

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