Formaldehyde → HCID 21091081, compound

HRID 351245Notes

Reaction equation

HRID 351245 reaction equation
[CH2:1]=O.[C:3]([BH3-])#[N:4].[Na+].N[C:8]1[CH:12]=[C:11]([C:13]2[CH:25]=[CH:24][C:16]([O:17][CH2:18][CH2:19][NH:20][C:21]([NH2:23])=[O:22])=[CH:15][CH:14]=2)[N:10]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)[N:9]=1>CO>[CH3:1][N:4]([CH3:3])[C:8]1[CH:12]=[C:11]([C:13]2[CH:25]=[CH:24][C:16]([O:17][CH2:18][CH2:19][NH:20][C:21]([NH2:23])=[O:22])=[CH:15][CH:14]=2)[N:10]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)[N:9]=1

Participants

5

Reactant 3

HCID 712Formaldehyde2×HCID 5003444Sodium cyanoborohydride2×HCID 21091065HCID 21091065, compound

Product 1

HCID 21091081HCID 21091081, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

37% aqueous solution of formaldehyde (0.23 ml) and sodium cyanoborohydride (53 mg) were added to a solution of N-(2-{4-[3-amino-1-(4-methoxyphenyl)-1H-pyrazol-5-yl]-phenoxy}ethyl)urea (103.1 mg) in MeOH (2 ml). The reaction mixture was stirred at ambient temperature for 3 hours. 37% aqueous solution of formaldehyde (0.23 ml) and sodium cyanoborohydride (53 mg) were added to the mixture and the reaction mixture was stirred at ambient temperature for 4 days. The mixture was concentrated in vacuo, and the residue was partitioned between ethyl acetate and H2O. The organic layer was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by preparative thin layer silica gel chromatography developed by CHCl3:MeOH:28% aqueous NH4OH=100:10:1. The separated silica gel was extracted with same solvent and the solvent was evaporated in vacuo to give N-(2-{4-[3-(dimethylamino)-1-(4-methoxyphenyl)-1-H-pyrazol-5-yl]phenoxy}ethyl)urea (59.9 mg) as an amorphous powder.

Workup

  1. stirringthe reaction mixture was stirred at ambient temperature for 4 days
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was partitioned between ethyl acetate and H2O
  4. washThe organic layer was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by preparative thin layer silica gel chromatography
  8. extractionThe separated silica gel was extracted with same solvent
  9. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-86fa22e2c8084ed1b32c007265196ce6
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

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