Potassium Hydroxide → HCID 71726519, compound

HRID 870922Notes

Reaction equation

HRID 870922 reaction equation
[NH2:1][C@@H:2]([CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]2[C:18]3[C:13](=[C:14]([NH:19]C(=O)C)[N:15]=[CH:16][CH:17]=3)[CH2:12][O:11][C:9]=2[CH:10]=1.[OH-].[K+]>C(O)C.O>[NH2:1][C@@H:2]([CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]2[C:18]3[C:13](=[C:14]([NH2:19])[N:15]=[CH:16][CH:17]=3)[CH2:12][O:11][C:9]=2[CH:10]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 71726518HCID 71726518, compound

Product 1

HCID 71726519HCID 71726519, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of (S)—N-(8-((2-amino-4-methylpentyl)oxy)-5H-chromeno[3,4-c]pyridin-4-yl)acetamide (20 mg, 0.056 mmol) (prepared as in Example 12, Part H) in a mixture of ethanol (10 mL) and water (2 mL) was added KOH (31.6 mg, 0.563 mmol) and the reaction was heated at 70° C. for 14 h. After completion of the reaction, the volatile organic solvent was removed under reduced pressure, water (20 mL) was added and the solution extracted with dichloromethane (2×20 mL). The combined organic extracts were washed with water (1×20 mL), dried over sodium sulfate and concentrated under reduced pressure to obtain (S)-8-((2-amino-4-methylpentyl)oxy)-5H-chromeno[3,4-c]pyridin-4-amine (2.31 mg, 7.15 umol, 13% yield) as an off-white solid. 1H NMR (400 MHz, MeOD) δ 7.90 (d, J=5.6 Hz, 1H), 7.69 (d, J=8.7 Hz, 1H), 6.98 (d, J=5.6 Hz, 1H), 6.72 (m, 1H), 6.6 (d, J=2.5 Hz, 1H), 5.07 (s, 2H), 4.10 (m, 1H), 3.92 (m, 1H), 3.40 (m, 1H), 1.82 (m, 1H), 1.49 (m, 2H), 1.01 (m, 6H); LCMS (ESI) m/e 314.2 [(M+H)+, calcd for C18H24N3O2 314.2]; LC/MS retention time (Method C): tR=1.21 min; HPLC retention time (method A): tR=7.52 min; HPLC retention time (method B): tR=8.68 min.

Workup

  1. customAfter completion of the reaction
  2. customthe volatile organic solvent was removed under reduced pressure, water (20 mL)
  3. additionwas added
  4. extractionthe solution extracted with dichloromethane (2×20 mL)
  5. washThe combined organic extracts were washed with water (1×20 mL)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6873aeabc46c4c019d5a9ba38779eedb
Source dataset
uspto-grants-2015_03
Patent number
US08969564B2

Reaction notes

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