Dimethylamine → HCID 69226827, compound

HRID 2253283Notes

Reaction equation

HRID 2253283 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=[C:11]([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]4[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30](=[O:32])[NH2:31])=[CH:24][CH:23]=4)=[CH:17][CH:16]=3)[C:12](O)=[O:13])=[CH:9][C:4]=2[O:3][CH2:2]1.[CH3:33][N:34](C=O)[CH3:35].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.CNC>>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=[C:11]([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]4[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30](=[O:32])[NH2:31])=[CH:24][CH:23]=4)=[CH:17][CH:16]=3)[C:12]([N:34]([CH3:35])[CH3:33])=[O:13])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 4

HCID 674DimethylamineHCID 6228DimethylformamideHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 69156452HCID 69156452, compound

Product 1

HCID 69226827HCID 69226827, compound

Procedure

To a solution of 3-benzo[1,3]dioxol-5-yl-2-{4-[4-(2-carbamoylethyl)-phenoxy]-phenyl}-acrylic acid, 78, (2.00 g, 4.6 mmol) in DMF (10 mL) triethylamine (0.96 mL, 6.9 mmol) and BOP reagent (2.21 g, 5.0 mmol) were added and stirred at room temperature for 15 min. Dimethylamine (2.0 M in THF, 6.90 mL, 1.8 mmol) was added and stirred for another 15 min. Reaction mixture was poured into ice cold water (100 mL) and extracted with ethyl acetate (4×50 mL). Combined organic layer was washed with saturated aqueous sodium bicarbonate solution (30 mL), water (3×50 mL), brine (2×50 mL), dried on anhydrous magnesium sulfate. Crude product was purified by silica gel chromatography and product was eluted with chloroform-methanol (19:1). Yield: 1.91 g (90.0%).

Workup

  1. stirringstirred for another 15 min
  2. customReaction mixture
  3. extractionextracted with ethyl acetate (4×50 mL)
  4. washCombined organic layer was washed with saturated aqueous sodium bicarbonate solution (30 mL), water (3×50 mL), brine (2×50 mL)
  5. dry with materialdried on anhydrous magnesium sulfate
  6. customCrude product was purified by silica gel chromatography and product
  7. washwas eluted with chloroform-methanol (19:1)

Sources & evidence

ORD record
ord-5bc0410194294f81b76e180f7201cfce
Source dataset
uspto-grants-2008_01
Patent number
US07323496B2

Reaction notes

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