Acetic Acid → HCID 178495915, compound

HRID 526745Notes

Reaction equation

HRID 526745 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH:13]=O)=[CH:11][NH:10][N:9]=2)=[CH:4][CH:3]=1.[CH3:15][O:16][CH:17]([O:21][CH3:22])[CH2:18][NH:19][CH3:20].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([CH2:13][N:19]([CH3:20])[CH2:18][CH:17]([O:21][CH3:22])[O:16][CH3:15])=[CH:11][NH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 85032,2-DimethoxyethylmethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 178519879HCID 178519879, compound

Product 1

HCID 178495915HCID 178495915, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 3-(4-fluorophenyl)-1H-pyrazole-4-carbaldehyde (3 g, 15.78 mmol, 1.00 equiv) and (2,2-dimethoxyethyl)(methyl)amine (2.3 g, 19.30 mmol, 1.22 equiv) in acetic acid (1.89 g, 31.47 mmol, 2.00 equiv) and 1,2-dichloroethane (30 mL) was stirred at room temperature for 30 min. Sodium triacetoxyborohydride (10 g) was then added and the resulting solution was stirred at room temperature for 3 h. The resulting mixture was washed with 2×20 mL of 5% potassium carbonate solution and 2×20 mL of brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum to give 3.29 g (71%) of N-((3-(4-fluorophenyl)-1H-pyrazol-4-yl)methyl)-2,2-dimethoxy-N-methylethanamine as a yellow oil. LCMS (method C, ESI): RT=0.63 min, m/z=294.0 [M+H]+.

Workup

  1. washThe resulting mixture was washed with 2×20 mL of 5% potassium carbonate solution and 2×20 mL of brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-557f05663693401d9da9c67b66ab84f7
Source dataset
uspto-grants-2016_05
Patent number
US09346761B2

Reaction notes

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