Hydrochloric Acid → HCID 44193055, compound

HRID 662111Notes

Reaction equation

HRID 662111 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:53][CH3:54])=[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:40]5[CH:45]=[CH:44][CH:43]=[C:42]([CH2:46][N:47]6[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]6)[CH:41]=5)[C:36]([CH3:39])=[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].[ClH:55]>C(O)C>[ClH:55].[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:53][CH3:54])=[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:40]5[CH:45]=[CH:44][CH:43]=[C:42]([CH2:46][N:47]6[CH2:48][CH2:49][NH:50][CH2:51][CH2:52]6)[CH:41]=5)[C:36]([CH3:39])=[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

4

Reactant 2

HCID 313Hydrochloric AcidHCID 44193054HCID 44193054, compound

Product 1

HCID 44193055HCID 44193055, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-N′-{[6-methyl-3′-(1-piperazinylmethyl)-3-biphenylyl]methyl}-2,6-pyridinedicarboxamide (565 mg, 0.774 mmol) in ethanol (1 mL) was added 1N HCl (0.735 mL, 0.735 mmol). The mixture was stirred at RT for 2 h. It was concentrated under vacuum. The residue was re-dissolved in ethanol and stripped down (this was repeated for three times). Then a 1:1 mixture of DCM:hexane (5 mL) was added and concentrated (this was repeated twice). Finally, the white solid that formed was dried under high vacuum for two days to give N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-N′-{[6-methyl-3′-(1-piperazinylmethyl)-3-biphenylyl]methyl}-2,6-pyridinedicarboxamide hydrochloride as a solid (530 mg, 89%). LC-MS m/z 730 (M+H)+, 0.79 min (ret time).

Workup

  1. concentrationIt was concentrated under vacuum
  2. dissolutionThe residue was re-dissolved in ethanol
  3. additionThen a 1:1 mixture of DCM
  4. additionhexane (5 mL) was added
  5. concentrationconcentrated (
  6. customFinally, the white solid that formed
  7. customwas dried under high vacuum for two days

Sources & evidence

ORD record
ord-a535f824faee4dbc8326ffc7e7507765
Source dataset
uspto-grants-2011_12
Patent number
US08084449B2

Reaction notes

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