Formaldehyde → 1-Cyclohexyl-4-methyl-7-{[2-(trimethylsilyl)ethoxy]methyl}-1,2,4,7-tetrahydropyrrolo[3',2':5,6]pyrido[4,3-d][1,3]oxazine

HRID 1506209Notes

Reaction equation

HRID 1506209 reaction equation
[CH:1]1([NH:7][C:8]2[C:13]([CH:14]([OH:16])[CH3:15])=[CH:12][N:11]=[C:10]3[N:17]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[CH:18]=[CH:19][C:9]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:28]=O.O>C(O)C>[CH:1]1([N:7]2[C:8]3[C:9]4[CH:19]=[CH:18][N:17]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:26])([CH3:25])[CH3:27])[C:10]=4[N:11]=[CH:12][C:13]=3[CH:14]([CH3:15])[O:16][CH2:28]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 962WaterHCID 712583901-(4-(Cyclohexylamino)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)ethanol

Product 1

HCID 712582801-Cyclohexyl-4-methyl-7-{[2-(trimethylsilyl)ethoxy]methyl}-1,2,4,7-tetrahydropyrrolo[3',2':5,6]pyrido[4,3-d][1,3]oxazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(4-(Cyclohexylamino)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)ethanol (9 mg, 0.02 mmol) and aqueous formaldehyde (35 wt %, 0.3 mL, 4 mmol) in ethanol (1 mL) were stirred at 75° C. for 1 hour. The reaction mixture was allowed to cool to room temperature and, after addition of water, extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting pale yellow oil (9 mg) containing the title compound was used for the next step without further purification.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. additionThe resulting pale yellow oil (9 mg) containing the title compound
  5. customwas used for the next step without further purification

Sources & evidence

ORD record
ord-75430822b4974942996cc95464e1ce03
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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