Formaldehyde → HCID 11575163, compound

HRID 1820151Notes

Reaction equation

HRID 1820151 reaction equation
[CH2:1]([O:4][C:5](=[O:28])[NH:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[C:18]([F:26])[CH:17]=2)=[CH:9][C:8]=1[CH3:27])[CH2:2][CH3:3].C=O.[C:31]([BH3-])#N.[Na+].O>CO>[CH2:1]([O:4][C:5](=[O:28])[NH:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([N:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:24])([F:25])[F:23])=[C:18]([F:26])[CH:17]=2)[CH3:31])=[CH:9][C:8]=1[CH3:27])[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 11545749HCID 11545749, compound

Product 1

HCID 11575163HCID 11575163, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

[4-(3-Fluoro-4-trifluoromethyl-benzylamino)-2,6-dimethyl-phenyl]-carbamic acid propyl ester (4f, 22 mg) and formaldehyde (0.1 mL) were refluxed in methanol (1 mL) for 3 hours. Sodium cyanoborohydride (35 mg) was added and the reaction mixture was stirred for 16 hours at 25° C., followed by addition of water (3 mL). The product was extracted with ethyl acetate (3×3 mL) and the combined organic phases were washed with brine (5 mL), dried over magnesium sulfate and concentrated in vacuo. The crude product was subjected to preparative LC-MS purification to furnish 9.7 mg (43% yield) of the title compound as a solid. LC-MS (m/z) 413 (MH+); tR=3.68, (UV, ELSD) 88%, 96%.

Workup

  1. extractionThe product was extracted with ethyl acetate (3×3 mL)
  2. washthe combined organic phases were washed with brine (5 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude product was subjected to preparative LC-MS purification

Sources & evidence

ORD record
ord-95e26dc364f7446d9a6b44740e1bfa23
Source dataset
uspto-grants-2009_10
Patent number
US07601870B2

Reaction notes

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