Diisopropylethylamine → HCID 58860825, compound

HRID 1350308Notes

Reaction equation

HRID 1350308 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8](/[C:11](=[CH:15]\[C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)/[C:12]([OH:14])=O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[Cl:46][C:47]1[S:51][C:50]([NH2:52])=[N:49][CH:48]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:46][C:47]1[S:51][C:50]([NH:52][C:12](=[O:14])/[C:11](/[C:8]2[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:10][CH:9]=2)=[CH:15]/[C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)=[N:49][CH:48]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1487432-Amino-5-chlorothiazole hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 21094118HCID 21094118, compound

Product 1

HCID 58860825HCID 58860825, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of (E)-2-(4-methanesulfonylphenyl)-3-thiophen-2-ylacrylic acid (Preparation 2, 309 mg, 1.0 mmol), HATU (813 mg, 2.1 mmol), 5-chlorothiazol-2-ylamine hydrochloride (258 mg, 1.5 mmol), and DIPEA (0.71 mL, 4.0 mmol) in anhydrous DMF (5 mL) was heated under microwave irradiation with stirring at 60° C. for 2 min. The solvents were evaporated off under reduced pressure, then the remainder was partitioned between CH2Cl2 (60 mL) and 1M HCl (60 mL). The organic layer was separated and washed with 1M HCl (60 mL), H2O (60 mL), saturated aqueous Na2CO3 (2×60 mL), H2O (60 mL), and brine (60 mL), before being dried (Na2SO4). Filtration, solvent evaporation, and flash chromatography (IH-EtOAc, 4:1 to 2:3) gave the title compound: RTA=3.77 min; m/z (ES+)=466.1 [M+MeCN+H]+.

Workup

  1. customThe solvents were evaporated off under reduced pressure
  2. customthe remainder was partitioned between CH2Cl2 (60 mL) and 1M HCl (60 mL)
  3. customThe organic layer was separated
  4. washwashed with 1M HCl (60 mL), H2O (60 mL), saturated aqueous Na2CO3 (2×60 mL), H2O (60 mL), and brine (60 mL)
  5. dry with materialbefore being dried (Na2SO4)
  6. filtrationFiltration, solvent evaporation, and flash chromatography (IH-EtOAc, 4:1 to 2:3)

Sources & evidence

ORD record
ord-1940ce4dac5b47cfb713a02d786765be
Source dataset
uspto-grants-2007_05
Patent number
US07214681B2

Reaction notes

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