Potassium Hydroxide → 3-(3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-6-phenyl-3H-imidazo[4,5-b]pyridin-2-amine

HRID 706491Notes

Reaction equation

HRID 706491 reaction equation
C(OC(=O)[NH:5][C:6]1[N:20]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]3[CH:31]=[N:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=3)=[C:24]([O:38][CH3:39])[CH:23]=2)[C:9]2=[N:10][CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:13]=[C:8]2[N:7]=1)C.[OH-].[K+]>C(O)CO.O>[CH3:39][O:38][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][C:25]=1[O:28][CH2:29][C:30]1[CH:31]=[N:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=1)[CH2:21][N:20]1[C:9]2=[N:10][CH:11]=[C:12]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:13]=[C:8]2[N:7]=[C:6]1[NH2:5]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 131733018HCID 131733018, compound

Product 1

HCID 1180098173-(3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-6-phenyl-3H-imidazo[4,5-b]pyridin-2-amineYield 34%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

To a stirred solution of ethyl(3-(3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-6-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)carbamate (0.090 g, 0.17 mmol) in ethylene glycol (10 mL) and water (10 mL) was added potassium hydroxide (1.00 g, 17.82 mmol). The mixture was heated to 100° C. After 48 h, the mixture was allowed to cool to room temperature and was diluted with water (30 mL). The mixture was extracted with dichloromethane (3×10 mL). The combined organic phases were dried over sodium sulfate, filtered, and concentrated. The residue was purified by prep-HPLC to afford 0.027 g (34%) of the product as a yellow solid: 1H NMR (500 MHz, CDCl3) δ 8.36 (s, 1H), 8.21 (s, 1H), 7.87 (s, 1H), 7.70-7.68 (m, 3H), 7.50 (s, 2H), 7.40 (s, 1H), 6.90-6.77 (m, 4H), 5.31 (s, 2H), 5.05 (s, 2H), 4.77 (s, 2H), 3.95 (s, 3H), 3.81 (s, 3H) ppm; (M+1)=468.

Workup

  1. temperatureto cool to room temperature
  2. extractionThe mixture was extracted with dichloromethane (3×10 mL)
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-309d1e9ed34b4d83b5eaa6dae9afd66c
Source dataset
uspto-grants-2015_11
Patent number
US09174986B2

Reaction notes

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