Dimethylamine → HCID 22398211, compound

HRID 1814796Notes

Reaction equation

HRID 1814796 reaction equation
[CH3:1][O:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[C:8]([OH:10])=O.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)[N:20]1[CH2:24]CC[CH2:21]1.CNC.C(N(C(C)C)CC)(C)C>C(#N)C>[CH3:21][N:20]([CH3:24])[C:8]([C:4]1[S:5][CH:6]=[CH:7][C:3]=1[O:2][CH3:1])=[O:10]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 14834753-Methoxythiophene-2-carboxylic acidHCID 2733179PyBroP

Product 1

HCID 22398211HCID 22398211, compoundYield 193.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 3-methoxythiophene carboxylic acid (1.84 g, 11.61 mmol), from step A, in 60 mL of acetonitrile at room temperature was added bromotripyrroli-dinophosphonium hexafluorophosphate (PyBrop, 5.40 g, 11.60 mmol), dimethyl amine (2.0 M in THF, 14.5 ml, 29.0 mmol) and diisopropylethyl amine (5.0 mL, 28.63 mmol) successively. After stirred for 1.5 day, the mixture was concentrated under reduced pressure to a yellow oil, which was purified by preparative TLC (CH2Cl2—MeOH=40:1). The silica was extracted with CH2Cl2 and methanol, the extracts were filtered and concentrated to an oil, which was further dried on high vacuum, yielding 4.16 g of N,N-dimethyl 3-methoxythiophene amide (contaminated by PyBrop impurity) (MH+=186.0).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure to a yellow oil, which
  2. customwas purified by preparative TLC (CH2Cl2—MeOH=40:1)
  3. extractionThe silica was extracted with CH2Cl2 and methanol
  4. filtrationthe extracts were filtered
  5. concentrationconcentrated to an oil, which
  6. customwas further dried on high vacuum

Sources & evidence

ORD record
ord-f39fcdfe8c574b5490acd009c24ef48f
Source dataset
uspto-grants-2005_04
Patent number
US06878709B2

Reaction notes

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