Hydrogen Peroxide → HCID 10277704, compound

HRID 456701Notes

Reaction equation

HRID 456701 reaction equation
[CH:1]1([NH:6][C:7]2[N:12]=[C:11]([C:13]3[N:17]4[CH:18]=[CH:19][CH:20]=[C:21]([N:22]5[CH2:27][CH2:26][O:25][CH2:24][CH2:23]5)[C:16]4=[N:15][C:14]=3[C:28]3[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][CH:29]=3)[CH:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-:36].[NH4+].OO>CO.O1CCCC1>[CH:1]1([NH:6][C:7]2[N:12]=[C:11]([C:13]3[N:17]4[CH:18]=[CH:19][CH:20]=[C:21]([N:22]5[CH2:27][CH2:26][O:25][CH2:24][CH2:23]5)[C:16]4=[N:15][C:14]=3[C:28]3[CH:29]=[CH:30][C:31]([C:32]([NH2:33])=[O:36])=[CH:34][CH:35]=3)[CH:10]=[CH:9][N:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 14923Ammonium HydroxideHCID 10205170HCID 10205170, compound

Product 1

HCID 10277704HCID 10277704, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a cold (0° C.) solution of 4-[3-[2-(cyclopentylamino)-4-pyrimidinyl]-8-(4-morpholinyl)imidazo[1,2-α]pyridin-2-yl]benzonitrile (16 mg, 0.03 mmol) in methanol (2 mL) and tetrahydrofuran (2 mL) was added concentrated ammonium hydroxide (1 mL, 28%) followed by hydrogen peroxide (0.1 mL, 30%). The cold bath was removed and the mixture was stirred at room temperature for 2 hours at which time an additional 0.1 mL of 30% hydrogen peroxide was added. After an additional 14 hours, the reaction was quenched by the addition of saturated aqueous sodium thiosulfate. Ether was added and the layers separated. The organic layer was washed with brine. The aqueous layer was extracted with ether and the combined organics were dried over magnesium sulfate. Filtration and concentration followed by flash chromatography (3% to 10% methanol in dichloromethane) provided 4-[3-[2-(cyclopentylamino)-4-pyrimidinyl]-8-(4-morpholinyl)imidazo[1,2-α]pyridin-2-yl]benzamide (17 mg, 99%) as a white solid. 1H NMR (CDCl3): δ 9.03 (broad, 1H), 8.15 (d, 1H), 7.89–7.82 (m, 4H), 6.85 (t, 1H), 6.64 (d, 1H), 6.44 (d, 1H), 6.22–5.79 (broad, 2H), 5.36 (m, 1H), 4.37 (m, 1H), 4.02 (m, 4H), 3.61 (m, 4H), 2.20–2.11 (m, 2H), 1.84–1.57 (m, 6H); MS m/z 484 (M+1).

Workup

  1. customThe cold bath was removed
  2. additionwas added
  3. waitAfter an additional 14 hours
  4. customthe reaction was quenched by the addition of saturated aqueous sodium thiosulfate
  5. additionEther was added
  6. customthe layers separated
  7. washThe organic layer was washed with brine
  8. extractionThe aqueous layer was extracted with ether
  9. dry with materialthe combined organics were dried over magnesium sulfate
  10. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-96df084ff4c64ea5b070675c919c5c1f
Source dataset
uspto-grants-2007_03
Patent number
US07186714B2

Reaction notes

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