Diisopropylethylamine → HCID 58487380, compound

HRID 2272250Notes

Reaction equation

HRID 2272250 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4](Cl)=[O:5].[CH3:12][C:13]1[O:14][C:15]2[CH:28]=[CH:27][CH:26]=[CH:25][C:16]=2[C:17]=1[C:18]1[N:19]=[CH:20][C:21]([NH2:24])=[N:22][CH:23]=1.CCN(C(C)C)C(C)C>ClCCl.O1CCCC1.CO.[OH-].[Na+]>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([NH:24][C:21]1[CH:20]=[N:19][C:18]([C:17]2[C:16]3[CH:25]=[CH:26][CH:27]=[CH:28][C:15]=3[O:14][C:13]=2[CH3:12])=[CH:23][N:22]=1)=[O:5]

Participants

8

Reactant 3

HCID 81531DiisopropylethylamineHCID 874382,6-Difluorobenzoyl chlorideHCID 58486692HCID 58486692, compound

Product 1

HCID 58487380HCID 58487380, compoundYield 54.7%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

Under an atmosphere of argon, 2,6-difluorobenzoyl chloride (8.0 mg, 35 μmol) was added to a stirred solution of 249 (13 mg, 0.1 mmol) and Hünig's base (37 μL, 28 mg, 0.2 mmol) in dichloromethane (0.5 mL) at room temperature. The reaction was stirred for 0.5 h. The solution was diluted with tetrahydrofuran (0.6 mL), methanol (0.3 mL) and 2 M sodium hydroxide solution (0.1 mL). The mixture was stirred and heated to 50° C. for 20 min then cooled to room temperature, diluted with dichloromethane (10 mL), dried with sodium sulfate and concentrated under reduced pressure. Flash chromatography (ISCO system, silica, 0-20% ethyl acetate in hexane) provided 250 (7.0 mg, 54%) as a solid: LRESIMS m/z 366.1 [M+H]+, calcd. for C20H14F2N3O2 366.1.

Workup

  1. stirringThe mixture was stirred
  2. temperaturethen cooled to room temperature
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b985e1f91dae4bd2a75a9d99762bc172
Source dataset
uspto-grants-2015_09
Patent number
US09120751B2

Reaction notes

Loading…