Isobutyraldehyde → HCID 66591554, compound

HRID 1261441Notes

Reaction equation

HRID 1261441 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][NH:15][CH2:16][C:17]([NH:19][CH3:20])=[O:18])=[CH:9][C:8]=1[O:21][CH3:22].[CH3:26][CH:27]([CH3:30])[CH:28]=O.[Cl:31]CCl.C(O)(=O)C>CO>[ClH:31].[F:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][N:15]([CH2:26][CH:27]([CH3:30])[CH3:28])[CH2:16][C:17]([NH:19][CH3:20])=[O:18])=[CH:9][C:8]=1[O:21][CH3:22]

Participants

5

Reactant 3

HCID 6561IsobutyraldehydeHCID 21922555Acetic acid methylene chlorideHCID 59596835HCID 59596835, compound

Product 1

HCID 66591554HCID 66591554, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

90 mg of 2-[2-[4-(3-Fluoro-benzyloxy)-3-methoxy-phenyl]-ethylamino]-N-methyl-acetamide (0.235 mmol) and 19 mg (0.263 mmol) of 2-methyl-propionaldehyde were dissolved in 6 ml of a dichloromethane/acetic acid (8:2, v:v) mixture and 1.5 ml of methanol. 100 mg (0.425 mmol) of (polystyrylmethyl)trimethylammonium cyanoborohydride (loading: 4.25 mmoUg) were added and the mixture was stirred at room temperature overnight. The resin was filtered and the solvent was removed. The crude product was purified by flash chromatography (dichloromethane/methanol/NH3 100:0:0→100:2:0.2 gradient v:v:v). The product was dissolved in anhydrous hydrochloric acid in ethyl acetate, the solvent was removed and the residue was triturated with diethyl ether. 80 mg (77% yield) of the title compound were isolated as a hygroscopic solid.

Workup

  1. filtrationThe resin was filtered
  2. customthe solvent was removed
  3. customThe crude product was purified by flash chromatography (dichloromethane/methanol/NH3 100:0:0→100:2:0.2 gradient v:v:v)
  4. dissolutionThe product was dissolved in anhydrous hydrochloric acid in ethyl acetate
  5. customthe solvent was removed
  6. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-94f64672341e4d039dc0ca77ae293548
Source dataset
uspto-grants-2013_06
Patent number
US08470877B2

Reaction notes

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