Formaldehyde → HCID 67431785, compound

HRID 1520230Notes

Reaction equation

HRID 1520230 reaction equation
[BH3-][C:2]#[N:3].[Na+].N[C:6]1[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][N:8]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[N:7]=1.[CH2:25]=O>C(O)(=O)C>[CH3:25][N:3]([CH3:2])[C:6]1[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][N:8]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[N:7]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 18002488Ethyl 3-amino-1-[(4-methoxyphenyl)methyl]-1H-pyrazole-4-carboxylate

Product 1

HCID 67431785HCID 67431785, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

According to Scheme 15 Step 2: NaBH3CN (7.26 mmol, 456 mg) was added to a solution of ethyl 3-amino-1-(4-methoxybenzyl)-1H-pyrazole-4-carboxylate (3.63 mmol, 1.00 g) and formaldehyde (109 mmol, 8.84 g) in acetic acid (10 mL). The reaction mixture was stirred for 4 hours at room temperature and was then extracted with AcOEt. After neutralization of the aqueous phase, it was extracted with AcOEt. The organic phase was dried over MgSO4, was filtered and was concentrated under reduced pressure. The crude product was purified by flash chromatography over silica gel using cyclohexane/AcOEt (90:10 to 0:100) as eluent to afford ethyl 3-(dimethylamino)-1-(4-methoxybenzyl)-1H-pyrazole-4-carboxylate (1.98 mmol, 600 mg, 54%) as an oil.

Workup

  1. extractionwas then extracted with AcOEt
  2. extractionAfter neutralization of the aqueous phase, it was extracted with AcOEt
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationwas filtered
  5. concentrationwas concentrated under reduced pressure
  6. customThe crude product was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-9972d22ecb854beebd80b79ddae020e0
Source dataset
uspto-grants-2015_07
Patent number
US09073907B2

Reaction notes

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