Diisopropylethylamine → HCID 67469166, compound

HRID 407112Notes

Reaction equation

HRID 407112 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].[Cl:12][C:13]1[C:14]([C:24]2[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=2)=[CH:15][C:16]2[O:20][C:19]([F:22])([F:21])[O:18][C:17]=2[CH:23]=1.CCN(C(C)C)C(C)C>ClCCl.O1CCCC1.CO.[OH-].[Li+]>[Cl:12][C:13]1[C:14]([C:24]2[CH:25]=[CH:26][C:27]([NH:28][C:4](=[O:5])[C:3]3[C:2]([F:1])=[CH:10][CH:9]=[CH:8][C:7]=3[F:11])=[CH:29][CH:30]=2)=[CH:15][C:16]2[O:20][C:19]([F:22])([F:21])[O:18][C:17]=2[CH:23]=1

Participants

8

Reactant 3

HCID 81531DiisopropylethylamineHCID 874382,6-Difluorobenzoyl chlorideHCID 67466812HCID 67466812, compound

Product 1

HCID 67469166HCID 67469166, compoundYield 33%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 3939Lithium HydroxideSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Under an atmosphere of argon, 2,6-difluorobenzoyl chloride (23 mg, 132 μmol) was added to a stirred solution of 89 (25 mg, 88 μmol) and Hünig's base (46 μL, 34 mg, 264 μmol) in dichloromethane (440 μL) at room temperature. The reaction was stirred for 0.5 h. The solution was diluted with tetrahydrofuran (1 mL), methanol (1 mL) and 1.2 M lithium hydroxide solution (0.5 mL). The mixture was stirred and heated to 60° C. for 10 min then cooled to room temperature, diluted with dichloromethane and dried with sodium sulfate. The mixture was concentrated under reduced pressure. Flash chromatography (ISCO system, silica, 0-20% ethyl acetate in hexane) provided 90 (12.2 mg, 33%) as a solid: LRESIMS m/z 424.1 [M+H]+, calcd. for C20H11Cl1F4N1O3 424.0.

Workup

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

Sources & evidence

ORD record
ord-091f8f81ea094ad084895971621892f4
Source dataset
uspto-grants-2014_06
Patent number
US08754219B2

Reaction notes

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