Hydrochloric Acid → HCID 68907177, compound

HRID 662123Notes

Reaction equation

HRID 662123 reaction equation
[C@H:1]12[CH2:7][C@H:4]([NH:5][CH2:6]1)[CH2:3][N:2]2[CH2:8][C:9]1[CH:10]=[C:11]([C:15]2[C:20]([CH3:21])=[CH:19][CH:18]=[C:17]([CH2:22][NH:23][C:24]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([NH:34][CH2:35][C:36]4[C:37]([NH:49][CH:50]5[CH2:55][CH2:54][O:53][CH2:52][CH2:51]5)=[C:38]5[CH:46]=[N:45][N:44]([CH2:47][CH3:48])[C:39]5=[N:40][C:41]=4[CH2:42][CH3:43])=[O:33])[N:27]=3)=[O:25])[CH:16]=2)[CH:12]=[CH:13][CH:14]=1.[ClH:56]>C(O)C>[ClH:56].[C@H:1]12[CH2:7][C@H:4]([NH:5][CH2:6]1)[CH2:3][N:2]2[CH2:8][C:9]1[CH:10]=[C:11]([C:15]2[C:20]([CH3:21])=[CH:19][CH:18]=[C:17]([CH2:22][NH:23][C:24]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([NH:34][CH2:35][C:36]4[C:37]([NH:49][CH:50]5[CH2:55][CH2:54][O:53][CH2:52][CH2:51]5)=[C:38]5[CH:46]=[N:45][N:44]([CH2:47][CH3:48])[C:39]5=[N:40][C:41]=4[CH2:42][CH3:43])=[O:33])[N:27]=3)=[O:25])[CH:16]=2)[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 44193148HCID 44193148, compound

Product 1

HCID 68907177HCID 68907177, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-({3′-[(1S,4S)-2,5-diazabicyclo[2.2.1]hept-2-ylmethyl]-6-methyl-3-biphenylyl}methyl)-N′-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-2,6-pyridinedicarboxamide (390 mg, 0.526 mmol) in ethanol 95 mL) was added 1N HCl (0.526 mL, 0.526 mmol). The mixture was stirred at RT for 2 h. It was concentrated under vacuum. The residue was re-dissolved in ethanol and it was evaporated (this was repeated three times). Then a 1:1 mixture of DCM:hexane (5 mL) was added and concentrated (this was repeated twice). Finally, the solid, a white material, was dried under high vacuum for two days to give N-({3′-[(1S,4S)-2,5-diazabicyclo[2.2.1]hept-2-ylmethyl]-6-methyl-3-biphenylyl}methyl)-N′-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-2,6-pyridinedicarboxamide hydrochloride as a solid (404 mg, 99%). LC-MS m/z 742 (M+H)+, 0.79 min (ret time).

Workup

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

Sources & evidence

ORD record
ord-d9ae08dadf9c4a11883682fd9edf8bec
Source dataset
uspto-grants-2011_12
Patent number
US08084449B2

Reaction notes

Loading…