Diisopropylethylamine → HCID 68756823, compound

HRID 2097999Notes

Reaction equation

HRID 2097999 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH3:10])[C:6]=1[C:7]([NH2:9])=[O:8].[I:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19](O)=[O:20])=[CH:14][CH:13]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[I:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([NH:1][C:2]2[S:3][CH:4]=[C:5]([CH3:10])[C:6]=2[C:7]([NH2:9])=[O:8])=[O:20])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1372144-Iodophenylacetic acidHCID 2938102-Amino-4-methylthiophene-3-carboxamideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 68756823HCID 68756823, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-4-methylthiophene-3-carboxamide (1 g, 6.4 mmol) and 2-(4-iodophenyl)acetic acid (1.83 g, 7.0 mmol) in methylene chloride (10 mL) was added Hunig's base (i.e., N,N-diisopropylethylamine) (30.1 mL, 18 mmol) and HATU (2.66 g, 7.0 mmol). The heterogeneous mixture was stirred for 18 h. The reaction was quenched by addition of saturated aqueous ammonium chloride solution and the biphasic mixture was extracted with additional methylene chloride. The organic layer was washed with brine, dried over sodium sulfate and concentrated under reduced pressure to provide a pale brown solid. LCMS method [2]: rt=2.02 min; M+Na 423.0. Material was used without further purification.

Workup

  1. customThe reaction was quenched by addition of saturated aqueous ammonium chloride solution
  2. extractionthe biphasic mixture was extracted with additional methylene chloride
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto provide a pale brown solid
  7. customrt=2.02 min
  8. customMaterial was used without further purification

Sources & evidence

ORD record
ord-3e24a695807c45eb89919fc3521f2fd6
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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