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Pyridinium chloride → (R)-2-(1-(3-amino-4-(naphthalen-2-yl)butanoyl)piperidin-3-yl)-3-(3-methoxypropyl)-3H-imidazo[4,5-b]pyridin-5(4H)-one

HRID 1096619
Notes
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Reaction equation

HRID 1096619 reaction equation
C[O:2][C:3]1[N:8]=[C:7]2[N:9]([CH2:41][CH2:42][CH2:43][O:44][CH3:45])[C:10]([CH:12]3[CH2:17][CH2:16][CH2:15][N:14]([C:18](=[O:40])[CH2:19][C@H:20]([NH:32]C(=O)OC(C)(C)C)[CH2:21][C:22]4[CH:31]=[CH:30][C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[CH:23]=4)[CH2:13]3)=[N:11][C:6]2=[CH:5][CH:4]=1.Cl.N1C=CC=CC=1>O>[NH2:32][CH:20]([CH2:21][C:22]1[CH:31]=[CH:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=1)[CH2:19][C:18]([N:14]1[CH2:15][CH2:16][CH2:17][C@@H:12]([C:10]2[N:9]([CH2:41][CH2:42][CH2:43][O:44][CH3:45])[C:7]3[NH:8][C:3](=[O:2])[CH:4]=[CH:5][C:6]=3[N:11]=2)[CH2:13]1)=[O:40]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 66785172(R)-tert-butyl 4-(3-(5-methoxy-3-(3-methoxypropyl)-3H-imidazo[4,5-b]pyridin-2-yl)piperidin-1-yl)-1-(naphthalen-2-yl)-4-oxobutan-2-ylcarbamate

Product 1

HCID 66784241(R)-2-(1-(3-amino-4-(naphthalen-2-yl)butanoyl)piperidin-3-yl)-3-(3-methoxypropyl)-3H-imidazo[4,5-b]pyridin-5(4H)-oneYield 3.5%

Reagents, catalysts & solvents 1

HCID 962Water
Solvent

Conditions

Temperature
150 °C

Procedure

(R)-tert-Butyl 4-(3-(5-methoxy-3-(3-methoxypropyl)-3H-imidazo[4,5-b]pyridin-2-yl)piperidin-1-yl)-1-(naphthalen-2-yl)-4-oxobutan-2-ylcarbamate (33E) (0.114 mmol, 0.070 g) prepared according to Example 33, Steps A-E and pyridine hydrochloride (8.65 mmol, 1.00 g) were added to a 15 mL round bottomed flask equipped for stirring under nitrogen. The reaction was subsequently heated to 150° C. and stirred for 15 min. The reaction was cooled to room temperature and water (2 mL) was added. The solution was stirred for 30 minutes at room temperature to allow the solid to completely dissolve. This solution was then filtered and directly purified by preparative LC/MS (10-50% CH3CN in H2O). The resultant fractions were collected and the solvent was removed in-vacuo affording the title compound as a clear colored oil (0.004 mmol, 0.002 g, 3% yield). ESI-MS: m/z 502.2 (M+H)+.

Workup

  1. additionwere added to a 15 mL round bottomed flask
  2. customequipped
  3. stirringstirred for 15 min
  4. temperatureThe reaction was cooled to room temperature
  5. stirringThe solution was stirred for 30 minutes at room temperature
  6. dissolutionto completely dissolve
  7. filtrationThis solution was then filtered
  8. customdirectly purified by preparative LC/MS (10-50% CH3CN in H2O)
  9. customThe resultant fractions were collected
  10. customthe solvent was removed in-vacuo

Sources & evidence

ORD record
ord-94d92af04a124997baacaf457b9881d4
Source dataset
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08138168B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes